A Homodinuclear Mn(III)2-Schiff Base Complex for Catalytic Asymmetric 1,4-Additions of Oxindoles to Nitroalkenes

被引：198

作者：

Kato, Yuko ^{[1
]}

Furutachi, Makoto ^{[1
]}

Chen, Zhihua ^{[1
]}

Mitsunuma, Harunobu ^{[1
]}

Matsunaga, Shigeki ^{[1
]}

Shibasaki, Masakatsu ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 26期

关键词：

ENANTIOSELECTIVE SYNTHESIS; ALPHA-ARYLATION; ADDITIONS; REARRANGEMENT;

D O I：

10.1021/ja903566u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic asymmetric 1,4-additions of 3-substituted oxindoles to beta-aryl, beta-heteroaryl, and beta-alkenyl nitroalkenes are described. A new homodinuclear Mn-2(OAc)(2)-Schiff base 1 complex was required to realize high diastereo- and enantioselectivity. Mn-2(OAc)(2)-1 (1-5 mol %) promoted the 1,4-additions in 99-83% yield, 96-85% ee, and >30:1-5:1 dr at room temperature, providing useful chiral building blocks for the synthesis of beta-aminooxindoles with vicinal quaternary/tertiary carbon stereocenters.

引用

页码：9168 / +

页数：3

共 32 条

[1] Catalysis of the Michael addition reaction by late transition metal complexes of BINOL-derived salens [J].

Annamalai, V ;

DiMauro, EF ;

Carroll, PJ ;

Kozlowski, MC .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1973-1981

[2]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

[3] Thiourea-Catalyzed Highly Enantio- and Diastereoselective Additions of Oxindoles to Nitroolefins: Application to the Formal Synthesis of (+)-Physostigmine [J].

Bui, Tommy ;

Syed, Salahuddin ;

Barbas, Carlos F., III .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8758-+

[4] A bench-stable homodinuclear Ni2-chiff base complex for catalytic asymmetric synthesis of α-tetrasubstituted anti-α,β-diamino acid surrogates [J].

Chen, Zhihua ;

Morimoto, Hiroyuki ;

Matsunaga, Shigeki ;

Shibasaki, Masakatsu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (07) :2170-+

[5] A Stable Homodinuclear Biscobalt(III)-Schiff Base Complex for Catalytic Asymmetric 1,4-Addition Reactions of β-Keto Esters to Alkynones [J].

Chen, Zhihua ;

Furutachi, Makoto ;

Kato, Yuko ;

Matsunaga, Shigeki ;

Shibasaki, Masakatsu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (12) :2218-2220

[6] Recent advances in metal-catalyzed asymmetric conjugate additions [J].

Christoffers, Jens ;

Koripelly, Girish ;

Rosiak, Anna ;

Roessle, Michael .

SYNTHESIS-STUTTGART, 2007, (09) :1279-1300

[7] Palladium-catalyzed enantioselective cyclization of silyloxy-1,6-enynes [J].

Corkey, Britton K. ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (10) :2764-+

[8] Catalytic asymmetric synthesis of quaternary carbons bearing two aryl substituents. Enantioselective synthesis of 3-alkyl-3-aryl oxindoles by catalytic asymmetric intramolecular Heck reactions [J].

Dounay, AB ;

Hatanaka, K ;

Kodanko, JJ ;

Oestreich, M ;

Overman, LE ;

Pfeifer, LA ;

Weiss, MM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6261-6271

[9] The asymmetric intramolecular Heck reaction in natural product total synthesis [J].

Dounay, AB ;

Overman, LE .

CHEMICAL REVIEWS, 2003, 103 (08) :2945-2963

[10] AcOLeDMAP and BnOLeDMAP: Conformationally Restricted Nucleophilic Catalysts for Enantioselective Rearrangement of Indolyl Acetates and Carbonates [J].

Duffey, Trisha A. ;

Shaw, Scott A. ;

Vedejs, Edwin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (01) :14-+

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