研究テーマ−ロジウム
触媒的不斉合成法の開発
CENTER>
Rh2(PTPA)4
不斉炭素
をもつ生物活性物質、特に医薬品の合成では、望みとする一方の鏡像異性体(光学異
性体)のみを完全な立体選択性で供給しなくてはなりません。少量の不斉源から大量
の光学活性物質を創り出す触媒的不斉合成は、最も効率の良い理想的供給法として学
術的にも、また、工業的にもその重要性を増しており、国内外で精力的な研究が展開
されています。私達は最近、光学活性N-フタロイルアミノ酸を架橋配位子と
する二核ロジウム(II)錯体を不斉触媒とする分子内環化反応が極めて高い立体選択性
で実現できることを見い出しました。錯体のX線結晶解析の結果から、反応部位に大
きく張り出したフタルイミド基が立体制御因子として機能し不斉空間を構築している
ものと推測されます。現在、本法を機軸とする各種生物活性物質の不斉合成を展開中
です。
二核ロジウム(II)錯体を触媒とする分子
内不斉C-H挿入反応
二核ロジウム(II)錯体を触
媒とする分子間不斉シクロプロパン化反応
二核ロジウム(II)錯体を触媒とする1,3双極付加環化反応
二核ロジウム(II)錯体を触媒とする[2,3]-シグマトロピー転位
二核ロジウム(II)錯体を触媒とするヘテロ
Diels-Alder反応
総説・著書
- ロジウム(II)
錯体を用いる不斉触媒反応. 橋本俊一, ファルマシア, 37, 1095 (2001).
- 金属カルベン中間体を経るイリド形成を機軸とする不斉触媒反応. 北垣伸治,
橋本俊一, 有機合成化学協会誌, 59,
1157 (2001).
- ロジウム(II)錯
体触媒を用いる不斉C-H挿入反応. 橋本俊一, 北垣伸治, "現代化学増刊36 生物
活性天然物の合成−複雑な構造をいかにして構築するか−",
桑島功, 伊藤嘉
彦, 奈良坂紘一, 鈴木啓介編, 東京化学同人, 2000, pp. 47.
- 高配位シリカー
トを経由する不斉Lewis塩基触媒反応, 中島 誠, 有機合成化学協会誌, 58, 839
(2000)
最近の発表論文
Diastereo- and Enantioselective Intramolecular 1,6-C-H Insertion Reactions of α-Diazo Esters Catalyzed by Chiral Dirhodium(II) Carboxylates
M. Ito, Y. Kondo, H. Nambu, M. Anada, K. Takeda, S. Hashimoto, Tetrahedron Lett., 2015, 56, 1397-1400. [DOI]
Asymmetric Total Synthesis of (-)-trans-Blechnic Acid via Rhodium(II)-Catalyzed C-H Insertion and Palladium(II)-Catalyzed C-H Olefination Reactions
M. Ito, R. Namie, J. Krishnamurti, H. Miyamae. K. Takeda, H. Nambu, S. Hashimoto, Synlett, ,2014, 25, 288-292. [DOI]
Enantio- and Diastereoselective Hetelo-Diels-Alder Reaction between 4-Methyl-Substituted Rawal's Diene and Aldehydes Catalyzed by Chiral Dirhodium(II) Carboxamidates: Catalytic Asymmetric Synthesis of (-)-cis-Aerangis Lactone
Y. Watanabe, N. Shimada, M. Anada, S. Hashimoto, Tetrahedron: Asymmetry, 2014, 25, 63-73. [DOI]
Enantioselective Cycloaddition of Carbonyl Ylides with Arylalenes using Rh2(S-TCPTTL)4
J. Krishnamurti, H. Nambu, K. Takeda, M. Anada, S. Hashimoto, Org. & Biomol. Chem., 2013, 11, 5374-5382. [DOI]
Catalytic Asymmetric Intermolecular C-H Insertion Reactions of 1,4-Cyclohexadiene with 2,4-Dimethyl-3-pentyl α-Alkyl-α-diazoacetates using Chiral Dirhodium(II) Carboxylates.
T. Goto, T. Onozuka, Y. Kosaka, M. Anada, K. Takeda and S. Hashimoto, Heterocycles, 2012, 86, 1647-1659. [DOI].
A Polymer-Supported Chiral Fluorinated Dirhodium(II) Complex for Asymmetric Amination of Silyl Enol Ethers.
T. Oohara, H. Nambu, M. Anada, K. Takeda and S. Hashimoto, Adv. Synth. Catal., 2012, 354(11-12), 2331-2338 [DOI].
Enantio- and Diastereoselective Hetero-Diels-Alder Reactions between 2-Aza-3-silyloxy-1,3-butadienes and Aldehydes Catalyzed by Chiral Dirhodium(II) Carboxamidates.
Y. Watanabe, T. Washio, J. Krishnamurthi, M. Anada and S. Hashimoto, Chem. Commun., 2012, 48(55), 6969-6971[DOI].
Catalytic Enantioselective Intermolecular Cycloaddition of Diazodiketoester-Derived Carbonyl Ylides with Indoles Using Chiral Dirhodium(II) Carboxylates.
N. Shimada, T. Oohara, J. Krishnamurthi, H. Nambu and S. Hashimoto, Org. Lett., 2011, 13, 6284-6287[DOI]. (Highlighted in Synfacts 2010, 1442)
Continuous Flow System with a Polymer-Supported Dirhodium(II) Catalyst: Application to Enantioselective Carbonyl Ylide Cycloaddition Reactions.
K. Takeda, T. Oohara, N. Shimada, H. Nambu and S. Hashimoto, Chem. Eur. J, 2011, 17, 13992-13998 [DOI].
Highly Enantioselective Cyclopropenation Reaction of 1-Alkynes with α-Alkyl-α-diazoesters Catalyzed by Dirhodium(II) Carboxylates.
T. Goto, K. Takeda, N. Shimada, H. Nambu, M. Anada, M. Shiro, K. Ando, and S. Hashimoto, Angew. Chem. Int. Ed., 2011, 50, 6803-6808 [DOI].
Catalytic Enantioselective C-H Functionalization of Indoles with α-Diazopropionates Using Chiral Dirhodium(II) Carboxylates: Asymmetric Synthesis of the (+)-α-Methyl-3-indolylacetic Acid Fragment of Acremoauxin A.
T. Goto, Y. Natori, K. Takeda, H. Nambu and S. Hashimoto, Tetrahedron: Asymmetry, 2011, 22, 907-915 [DOI].
3. Enantio- and Diastereoselective Cyclopropanation with tert-Butyl α-Diazopropionate Catalyzed by Dirhodium(II) Tetrakis[N-tetrabromophthaloyl-(S)-tert-leucinate].
T. Goto, K. Takeda, M. Anada, K. Ando and S. Hashimoto, Tetrahedron Lett., 2011, 52, 4200-4203 [DOI].
A Short Catalytic Asymmetric Synthesis of Diospongins A and B via a One-pot Sequential Hetero-Diels-Alder/Mukaiyama-Michael Reaction Process.
M. Anada, T. Washio, Y. Watanabe, K. Takeda, and S. Hashimoto, Eur. J. Org. Chem., 2010, (35), 6850-6854 [DOI].
Catalytic Asymmetric Synthesis of Descurainin via 1,3-Dipolar Cycloaddition of a Carbonyl Ylide using Rh2(R-TCPTTL)4.
N. Shimada, T. Hanari, Y. Kurosaki, M. Anada, H. Nambu, and S. Hashimoto, Tetrahedron Lett., 2010, 51(50), 6572-6575.[DOI].
A Polymer-Supported Chiral Dirhodium(II) Complex: Highly Durable and Recyclable Catalyst for Asymmetric Intramolecular C-H Insertion Reactions.
K. Takeda, T. Oohara, M. Anada, H. Nambu, and S. Hashimoto, Angew. Chem. Int. Ed., 2010, 49(39), 6979-6983.[DOI].
Catalytic Asymmetric Synthesis of the endo-6-Aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one Natural Product from Ligusticum Chuanxing via 1,3-Dipolar Cycloaddition of a Formyl-Derived Carbonyl Ylide Using Rh2(S-TCPTTL)4.
N. Shimada, T. Hanari, Y. Kurosaki, K. Takeda, M. Anada, H. Nambu, M. Shiro, and S. Hashimoto, J. Org. Chem., 2010, 75(17), 6039-6042.[DOI]. (Highlighted in Synfacts 2010, 1329)
Asymmetric Intermolecular N-H Insertion Reaction of Phenyldiazoacetates with Anilines Catalyzed by Achiral Dirhodium(II) Carboxylates and Cinchona Alkaloids.
H. Saito, T. Uchiyama, M. Miyake, M. Anada, S. Hashimoto, T. Takabatake, and S. Miyairi, Heterocycles, 2010, 81(5), 1149-1155.[Abstract].
Catalytic Asymmetric Construction of the 7-exo-Aryl-6,8-dioxabicyclo[3.2.1]octane Framework of Psoracorylifols B and C Using a Carbonyl Ylide Cycloaddition Strategy.
Y. Kurosaki, N. Shimada, M. Anada, H. Nambu, and S. Hashimoto, Bull. Korean Chem. Soc., 2010, 31(3), 694-696.[DOI].
The Mukaiyama Aldol and Mukaiyama-Michael Reaction Promoted by Commercially Available Molecular Sieves.
M. Anada, T. Washio, Y. Watanabe, and S. Hashimoto, Heterocycles, 2010, 80(2), 1489-1503.[Abstract].
Highly Enantioselective Hetero-Diels-Alder Reactions between Rawal's Diene and Aldehydes Catalyzed by Chiral Dirhodium(II) Carboxamidates.
Y. Watanabe, T. Washio, N. Shimada, M. Anada, and S. Hashimoto, Chem. Commun., 2009, (47), 7294-7296.[DOI]. (Highlighted in Synfacts 2010, 324)
Asymmetric Synthesis of Neolignans (-)-epi-Conocarpan and (+)-Conocarpan via Rh(II)-Catalyzed C-H Insertion Process and Revision of the Absolute Configuration of (-)-epi-Conocarpan.
Y. Natori, H. Tsutsui, N. Sato, S. Nakamura, H. Nambu, M. Shiro, and S. Hashimoto, J. Org. Chem., 2009, 74 (11), 4418-4421.[DOI].
Enantioselective Construction of 2,8-Dioxabicyclo[3.2.1]octane Ring System via [2,3]-Sigmatropic Rearrangement of Oxonium Ylide Using Chiral Dirhodium(II) Carboxylates.
N. Shimada, S. Nakamura, M. Anada, M. Shiro, and S. Hashimoto, Chem. Lett., 2009, 38 (5), 488-489.[DOI].
Asymmetric Approach to the Pentacyclic Skeleton of Aspidosperma Alkaloids via Enantioselective Intramolecular 1,3-Dipolar Cycloaddition of Carbonyl Ylides Catalyzed by Chiral Dirhodium(II) Carboxylates.
H. Nambu, M. Hikime, J. Krishnamurthi, M. Kamiya, N. Shimada, and S. Hashimoto, Tetrahedron Lett., 2009, 50 (26), 3675-3678.[DOI]
Asymmetric Formal Synthesis of (-)-Pancracine via Catalytic Enantioselective C-H Amination Process.
M. Anada, M. Tanaka, N. Shimada, H. Nambu, M. Yamawaki, and S. Hashimoto, Tetrahedron, 2009, 65, 3069-3077.[DOI]
Catalytic Asymmetric Synthesis of (-)-Ritodrine Hydrochloride via Silyl Enol Ether Amination Using Dirhodium(II) Tetrakis[tetrafluorophthaloyl-(S)-tert-leucinate].
M. Tanaka, S. Nakamura, M. Anada, and S. Hashimoto, Heterocycles, 2008, 76, 1633-1645.[Abstract].
Catalytic Enantioselective Intermolecular Cycloaddition of 2-Diazo-3,6-diketoester-Derived Carbonyl Ylides with Alkynes and Styrenes Using Chiral Dirhodium(II) Carboxylates.
N. Shimada, M. Anada, S. Nakamura, H. Nambu, H. Tsutsui, and S. Hashimoto, Org. Lett, 2008, 10, 3603-3606.[DOI] (Highlighted in Synfacts 2008, 1069)
Catalytic Enantioselective Amination of Silyl Enol Ethers Using Chiral Dirhodium(II) Carboxylates: Asymmetric Formal Synthesis of (-)-Metazocine.
M. Anada, M. Tanaka, T. Washio, M. Yamawaki, T. Abe, and S. Hashimoto, Org. Lett, 2007, 9, 4559-4562.[DOI] (Highlighted in Synfacts 2008, 63)
Enantioselective amination of silylketene acetals with (N-arylsulfonylimino)phenyliodinanes catalyzed by chiral dirhodium(II) carboxylates: asymmetric synthesis of phenylglycine derivatives.
M. Tanaka, Y. Kurosaki, T. Washio, M. Anada, and S. Hashimoto, Tetrahedron Lett., 2007, 48, 8799-8802.[DOI]
Asymmetric syntheses of diarylheptanoid natural products (-)-centrolobine and (-)-de-O-methylcentrolobine via hetero-Diels-Alder reaction catalyzed by dirhodium(II) tetrakis[(R)-(benzene-fused-phthalimido)-2-piperidinonate].
T. Washio, R. Yamaguchi, T. Abe, H. Nambu, M. Anada, and S. Hashimoto, Tetrahedron, 2007, 63, 12037-12046.[DOI]
Catalytic Asymmetric Hetero-Diels-Alder Route to a Key Intermediate for the Synthesis of Calyxin L.
T. Washio, H. Nambu, M. Anada, and S. Hashimoto, Tetrahedron: Asymmetry, 2007, 18, 2606-2612.[DOI]
Catalytic Enantioselective Aziridination of Alkenes Using Chiral Dirhodium(II) Carboxylates.
M. Yamawaki, M. Tanaka, T. Abe, M. Anada, and S. Hashimoto, Heterocyles, 2007, 72, 709.[Abstract][HUSCAP(PDF)]
Chiral Phosphine Oxide BINAPO as a Lewis Base Catalyst for Asymmetric Allylation and Aldol Reaction of Trichlorosilyl Compounds.
S. Kotani, S. Hashimoto, and M. Nakajima, Tetrahedron, 2007, 63, 3122.[DOI]
Catalytic Enantioselective Tandem Carbonyl Ylide Formation/1,3-Dipolar Cycloaddition Reactions of α-Diazo Ketones with Aromatic Aldehydes Using Dirhodium(II) Tetrakis[N-benzene-fused-phthaloyl-(S)-valinate].
H. Tsutsui, N. Shimada, M. Anada, M. Nakajima, S. Nakamura, H. Nambu, and S. Hashimoto, Adv. Synth. Catal., 2007, 349, 521. [DOI] (Highlighted in Synfacts 2007, 827)
Enantioselective Synthesis of 3-Arylindan-1-ones via Intramolecular C-H Insertion Reactions of α-Diazo-β-ketoesters Catalyzed by Chiral Dirhodium(II) Carboxylates.
Y. Natori, M. Anada, S. Nakamura, H. Nambu, and S. Hashimoto, Heterocyles, 2006, 70, 635.[Abstract][HUSCAP(PDF)]
Enantioselective Intramolecular C-H Amidation of Sulfamate Esters Catalyzed by Chiral Dirhodium(II) Carboxylates.
M. Yamawaki, S. Kitagaki, M. Anada, and S. Hashimoto, Heterocyles, 2006, 69, 527.[Abstract][HUSCAP(PDF)]
Dirhodium(II) Tetrakis(perfluorobutyrate)-catalyzed 1,4-Hydrosilylation of α,β-Unsaturated Carbonyl Compounds.
M. Anada, M. Tanaka, K. Suzuki, H. Nambu, and S. Hashimoto, Chem. Pharm. Bull, 2006, 54, 1622.[PDF][HUSCAP(PDF)]
Enantioselective Aldol Reactions of Trichlorosilyl Enol Ethers Catalyzed by the Chiral Phosphine Oxide BINAPO.
S. Kotani, S. Hashimoto, and M. Nakajima, Synlett, 2006, 1116.[DOI]
Chiral Base-Catalyzed Aldol Reaction of Trimethoxysilyl Enol Ethers: Effect of Water as an Additive on Stereoselectivities.
Y. Orito, S. Hashimoto, T. Ishizuka, and M. Nakajima, Tetrahedron, 2006, 62, 390.[DOI]
Dirhodium(II) Tetrakis[N-benzene-fused Phthaloyl-(S)-piperidinonate] as Chiral Lewis Acid: Catalytic Enantioselective Aldol Reactions of Acetate-derived Silylketene Acetals and Aldehydes.
T. Washio, S. Nakamura, M. Anada, and S. Hashimoto, Heterocycles, 2005, 66, 567.[Abstract][HUSCAP(PDF)]
Practical Synthesis of Dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate].
H. Tsutsui, T. Abe, S. Nakamura, M. Anada, and S. Hashimoto, Chem. Pharm. Bull., 2005, 53, 1366. [PDF][HUSCAP(PDF)]
Highly Enantio- and Diastereoselective Construction of 1,2-Disubstituted Cyclopentane Compounds by Dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate]-Catalyzed C-H Insertion Reactions of α-Diazo Esters.
K. Minami, H. Saito, H. Tsutsui, H. Nambu, M. Anada, and S. Hashimoto, Adv. Synth. Catal., 2005, 347, 1483. [DOI][HUSCAP(PDF)](Highlighted in Synfacts 2006, 45)
Asymmetric Ring Opening of meso-Epoxides Catalyzed by the Chiral Phosphine Oxide BINAPO.
E. Tokuda, S. Kotani, H. Matsunaga, T. Ishizuka, S. Hashimoto, and M. Nakajima, Tetrahedron: Asymmetry, 2005, 16, 2391. [DOI]
Chiral Phosphine Oxide BINAPO as a Catalyst for Enantioselective Allylation of Aldehydes with Allyltrichlorosilanes.
M. Nakajima, S. Kotani, T. Ishizuka, and S. Hashimoto, Tetrahedron Lett., 2005, 46, 157. [DOI]
Enantioselective Aldol Reaction of Trimethoxysilyl Enol Ether Catalyzed by Lithium Binaphtholate.
M. Nakajima, Y. Orito, T. Ishizuka, and S. Hashimoto, Org. Lett., 2004, 6, 3763.[DOI]
A New Dirhodium(II) Carboxamidate Complex as a Chiral Lewis
Acid Catalyst for Enantioselective Hetero-Diels-Alder Reactions.
M. Anada, and T. Washio, and N. Shimada, and S. Kitagaki, and
M. Nakajima, and M. Shiro, and S. Hashimoto, Angew. Chem.
Int. Ed., 2004, 43, 2665.[DOI]
Enantioselective Aldol Reactions of Trichlorosilyl Enol Ethers
Catalyzed by Chiral N,N'-Dioxides and Monodentate N-Oxides.
M. Nakajima, T. Yokota, M. Saito, and S. Hashimoto, Tetrahedron
Lett., 2004, 45, 61.[DOI]
Chiral N-Oxides as Catalysts or Ligands in Enantioselective
Reactions.
M. Nakajima, J. Synth. Org. Chem. Jpn., 2003, 61,
1081.
Synthesis and Evaluation of Novel Dirhodium(II) Carboxylate
Catalysts with Atropisomeric Biaryl Backbone.
K. Hikichi, and S. Kitagaki, and M. Anada, and S. Nakamura, and
M. Nakajima, and M. Shiro, and S. Hashimoto, Heterocycles,
2003, 61, 391.[Abstract]
Enantioselective Michael Additions of β-Keto
Esters to α,β-Unsaturated
Carbonyl Compounds Catalyzed by a Chiral Biquinoline N,N'-Dioxide-scandium
Trifluoromethanesulfonate Complex.
M. Nakajima, S. Yamamoto, Y. Yamaguchi, S. Nakamura, and S. Hashimoto,
Tetrahedron, 2003, 59, 7307.[DOI]
Dirhodium(II) Tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate]:
an Exceptionally Effective Rh(II) Catalyst for Enantiotopically
Selective Aromatic C-H Insertions of Diazo Ketoesters.
H. Tsutsui, Y Yamaguchi, S. Kitagaki, S. Nakamura, M. Anada and
S. Hashimoto, Tetrahedron: Asymmetry, 2003, 14,
817.[DOI]
Dirhodium(II) Tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate]:
a New Chiral Rh(II) Catalyst for Enantioselective Amidation of
C-H Bonds:
M. Yamawaki, H. Tsutsui, S. Kitagaki, M. Anada, and S. Hashimoto,
Tetrahedron Lett., 2002, 43, 9561.[DOI]
Enantioselective Ring Opening of meso-Epoxides with
Tetrachlorosilane Catalyzed by Chiral Bipyridine N,N'-Dioxide
Derivatives.
M. Nakajima, M. Saito, M. Uemura, and S. Hashimoto, Tetrahedron
Lett., 2002, 43, 8827.[DOI]
Selective Synthesis of Optically Active Allenic and Homopropargylic
Alcohols from Propargyl Chloride.
M. Nakajima, M. Saito, and S. Hashimoto, Tetrahedron: Asymmetry,
2002, 13, 2449.[DOI]
Enantio- and Diastereoselective Synthesis of cis-2-Aryl-3-methoxycarbonyl-2,3-dihydrobenzofurans
via the Rh(II)-Catalyzed C-H Insertion Process.
H. Saito, H. Oishi, S. Kitagaki, S. Nakamura, M. Anada, and S.
Hashimoto, Org. Lett., 2002, 4, 3887.[DOI]
Enantioselective Tandem Formation and [2,3]-Sigmatropic Rearrangement
of Cyclic Propargylic Oxonium Ylides Catalyzed by Dirhodium(II)
Tetrakis[N-phthaloyl-(S)-tert-leucinate].
H. Tsutsui, M. Matsuura, K. Makino, S. Nakamura, M. Nakajima, S. Kitagaki,
and S. Hashimoto, Isr. J. Chem., 2001, 41,
283.
Catalytic Asymmetric Synthesis of 1,1'-Spirobiindan-3,3'-dione
via a Double Intramolecular C-H Insertion Process.
T. Takahashi, H. Tsutsui, M. Tamura, S. Kitagaki, M. Nakajima,
and S. Hashimoto, Chem. Commun., 2001, 1604.[DOI]
Enantioselective Michael Addition of β-Keto
Esters to Methyl Vinyl Ketone Employing a Chiral N,N'-Dioxide-scandium
Trifluoromethanesulfonate Complex as a Catalyst.
M. Nakajima, Y. Yamaguchi, and S. Hashimoto, Chem. Commun.,
2001, 1596.[DOI]
Enantioselective [2,3]-Sigmatropic and [1,2]-Stevens Rearrangements
via Intramolecular Formation of Allylic Oxonium Ylides Catalyzed
by Chiral Dirhodium(II) Carboxylates.
S. Kitagaki, Y. Yanamoto, H. Tsutsui, M. Anada, M. Nakajima,
and S. Hashimoto, Tetrahedron Lett., 2001, 42,
6361.[DOI]
Enantiocontrol in Tandem Allylic Sulfonium Ylide Generation
and [2,3]-Sigmatropic Rearrangement Catalyzed by Chiral Dirhodium(II)
Complexes.
S. Kitagaki, Y. Yanamoto, H. Okubo, M. Nakajima, and S. Hashimoto,
Heterocycles, 2001, 54, 623.[Abstract]
Enantioselective Si-H Insertion of Methyl Phenyldiazoacetate
Catalyzed by Dirhodium(II) Carboxylates Incorporating N-Phthaloyl-(S)-amino
Acids as Chiral Bridging Ligands.
S. Kitagaki, M. Kinoshita, M. Takeba, M. Anada, and S. Hashimoto,
Tetrahedron: Asymmetry, 2000, 11, 3855.[DOI]
Enantioselective Conjugate Addition of Thiols to Cyclic Enones
and Enals Catalyzed by Chiral N,N'-Dioxide-Cadmium Iodide
Complex.
M. Saito, M. Nakajima, and S. Hashimoto, Tetrahedron,
2000, 56, 9589.[DOI]
Enantioselective Intermolecular 1,3-Dipolar Cycloaddition
via Ester-derived Carbonyl Ylide Formation Catalyzed by Chiral
Dirhodium(II) Carboxylates.
S. Kitagaki, M. Yasugahira, M. Anada, M. Nakajima, and S. Hashimoto,
Tetrahedron Lett., 2000, 41, 5931.[DOI]
Enantioselective Conjugate Addition of Thiols to Enones and
Enals Catalyzed by Chiral N-Oxide-Cadmium Complex.
M. Saito, M. Nakajima, and S. Hashimoto, Chem. Commun,
2000, 1851.[DOI]
Double Stereodifferentiation in Intramolecular C-H Insertion
Reaction toward the Synthesis of 1β-Methylcarbapenem
Antibiotics.
M. Anada, S. Kitagaki, and S. Hashimoto, Heterocycles,
2000, 52, 875.[Abstract]
One-pot Enantioselective Synthesis of Optically Active Homoallylic
Alcohols from Allyl Halides and Aldehydes.
M. Nakajima, M. Saito, and S. Hashimoto, Chem. Pharm. Bull.,
2000, 48, 306.[Abstract]
Catalytic Enantioselective Synthesis of the Phosphodiesterase
Type IV Inhibitor (R)-(-)-Rolipram via Intramolecular
C-H Insertion Process.
M. Anada, O. Mita, H. Watanabe, S. Kitagaki, and S. Hashimoto,
Synlett , 1999, 1775.[DOI]
Enantiocontrol in Tandem Carbonyl Ylide Formation and Intermolecular
1,3-Dipolar Cycloaddition of α-Diazo
Ketones Mediated by Chiral Dirhodium(II) Carboxylate Catalyst.
S. Kitagaki, M. Anada, O. Kataoka, K. Matsuno, C. Umeda, N. Watanabe,
and S. Hashimoto, J. Am. Chem. Soc., 1999, 121,
1417.[DOI]
Enantioselective Synthesis of Binaphthol Derivatives by Oxidative
Coupling of Naphthol Derivatives Catalyzed by Chiral Diamine-Copper
Complexes.
M. Nakajima, I. Miyoshi, K. Kanayama, S. Hashimoto, M. Noji,
and K. Koga, J. Org. Chem., 1999, 64, 2264.[DOI]
A Concise Synthesis of (+)-α-Allokainic
Acid via Site- and Diastereoselective Intramolecular C-H Insertion
Process.
M. Anada, T. Sugimoto, N. Watanabe, M. Nakajima, and S. Hashimoto,
Heterocycles, 1999, 50, 969.[Abstract]
Aerobic Oxidative
Coupling of 2-Naphthol Derivatives Catalyzed
by a Copper-Amine Complex
without Solvent.
M. Nakajima, S. Hashimoto, M. Noji, and K. Koga,
Chem. Pharm.
Bull., 1998, 46, 1814. [DOI]
Enantioseletive Intramolecular C-H Insertion Route to a Key
Intermediate for the Synthesis of Trinem Antibiotics.
M. Anada and S.
Hashimoto, Tetrahedron Lett., 1998,[DOI]
39, 9063.
(S)-3,3'-Dimethyl-2,2'-biquinoline N,N'-Dioxide
as an
Efficient Catalyst for Enantioselective Addition of Allyltrichlorosilanes
to Aldehydes.
M. Nakajima, M. Saito, M. Shiro, and S. Hashimoto, J.
Am.
Chem. Soc., 1998, 120, 6419. [DOI]
Highly
Enantioselective Construction of the Key Azetidin-2-ones
for the Synthesis
of Carbapenem Antibiotics via Intramolecular
C-H Insertion Reactions of
a-Methoxycarbonyl-a-diazoacetamides Catalysed by Chiral Dirhodium(II)
Carboxylates.
M. Anada, N. Watanabe, and S. Hashimoto, Chem.
Commun.,
1998, 1517. [DOI]
Enantioselective Synthesis of
4-Substituted 2-Pyrrolidinones
by Site-selective C-H Insertion of a-Methoxycarbonyl-a-diazoacetanilides Catalyzed by Dirhodium(II)
Tetrakis[N-phthaloyl-(S)-tert-leucinate].
M.
Anada and S. Hashimoto, Tetrahedron Lett., 1998,
39,
79. [DOI]
Bipyridine N,N'-Dioxide: A Felicitous Ligand for
Methyltrioxorhenium-Catalyzed
Epoxidation of Olefins with Hydrogen
Peroxide.
M. Nakajima, Y. Sasaki, H. Iwamoto, and S. Hashimoto,
Tetrahedron
Lett., 1998, 39, 87. [DOI]
A Novel
Axially Dissymmetric Chiral Ligand Based on Amine
N-Oxide:
(R)- and (S)-3,3'-Dimethyl-2,2'-biquinoline
N,N'-Dioxide.
M. Nakajima, Y. Sasaki, M. Shiro, and S.
Hashimoto, Tetrahedron:
Asymmetry, 1997, 8, 341. [DOI]
Highly Enantioselective Intermolecular Cyclopropanation Catalyzed
by
Dirhodium(II) Tetrakis[3(S)-phthalimido-2-piperidonate]:
Solvent
Dependency of the Enantioselection.
S. Kitagaki, H. Matsuda, N.
Watanabe, and S. Hashimoto, Synlett,
1997, 1171. [DOI]
Site-
and Enantiocontrol in Intramolecular C-H Insersion
Reactions of a-Diazo Carbonyl Compounds
Catalyzed by DirhodiumC
arboxylates.
S. Hashimoto, N. Watanabe, M. Anada, and S. Ikegami,
J. Synth.
Org. Chem. Jpn., 1996, 54, 988. [DOI]
Dirhodium(II) Tetrakis[3(S)-phthalimido-2-piperidinonate]:
A
Novel Dirhodium(II) Carboxamidate Catalyst for Asymmetric
Cyclopropanation.
N. Watanabe, H. Matsuda, H. Kuribayashi, and S.
Hashimoto, Heterocycles,
1996, 42, 537. [DOI]
Dirhodium(II)
Tetrakis[N-phthaloyl-(S)-tert-leucinate]:
A Notable
Catalyst for Enantiotopically Selective Aromatic Substitution
Reactions of
a-Diazocarbonyl Compounds.
N. Watanabe, T.
Ogawa, Y. Ohtake, S. Ikegami, and S. Hashimoto,
Synlett,
1996, 85. [DOI]
Asymmetric Creation of Quaternary Carbon Centers by
Enantiotopically
Selective Aromatic C-H Insertion Catalyzed by Chiral
Dirhodium(II)
Carboxylates.
N. Watanabe, Y. Ohtake, S. Hashimoto, M.
Shiro, and S. Ikegami,
Tetrahedron Lett., 1995,
36, 1491. [DOI]
Catalytic Asymmetric Synthesis of Binaphthol
Derivatives
by Aerobic Oxidative Coupling of 3-Hydroxy-2-naphthoates with
Chiral Diamine-Copper Complex.
M. Nakajima, K. Kanayama, I. Miyoshi,
and S. Hashimoto, Tetrahedron
Lett., 1995, 36,
9519. [DOI]
Enantioselective Intramolecular C-H Insertion Reactions of
N-Alkyl-N-tert-Butyl-a-Methoxycarbonyl-a-Diazoacetamides Catalyzed by Dirhodium(II)
Carboxylates: Catalytic, Asymmetric Construction of 2-Azetidinones.
N.
Watanabe, M. Anada, S. Hashimoto, and S. Ikegami, Synlett,
1994, 1031. [DOI]
Double Asymmetric Induction in Intramolecular C-H
Insertion
Reactions of a-Diazo b-Keto
Esters.
S. Hashimoto, N. Watanabe, K.
Kawano, and S. Ikegami, Synth.
Commun., 1994,
24, 3277. [DOI]
Enantioselective Intramolecular C-H Insertion
Reactions of
a-Diazo b-Keto
Esters Catalyzed by Dirhodium(II)
Tetrakis[N-phthaloyl-(S)-phenylalaninate]:
The Effect of the
Substituent at the Insertion Site on Enantioselectivity.
S. Hashimoto,
N. Watanabe, and S. Ikegami, Synlett, 1994,
353. [DOI]
A New
Catalytic System for Aerobic Oxidative Coupling of
2-Naphthol Derivatives
by the Use of CuCl-Amine Complex: A Practical
Synthesis of Binaphthol
Derivatives.
M. Noji, M. Nakajima, and K. Koga, Tetrahedron
Lett.,
1994, 35, 7983. [DOI]
Enhancement of
Enantioselectivity in Intramolecular C-H Insertion
Reactions of a-Diazo b-Keto
Esters
Catalyzed by Chiral Dirhodium(II) Carboxylates.
S. Hashimoto, N.
Watanabe, T. Sato, M. Shiro, and S. Ikegami,
Tetrahedron
Lett., 1993, 34, 5109. [DOI]
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