Catalytic Asymmetric Synthesis of 3-Aminooxindoles: Enantiofacial Selectivity Switch in Bimetallic vs Monometallic Schiff Base Catalysis

被引：249

作者：

Mouri, Shinsuke ^{[1
]}

Chen, Zhihua ^{[1
]}

Mitsunuma, Harunobu ^{[1
]}

Furutachi, Makoto ^{[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 | 2010年 / 132卷 / 04期

关键词：

BETA-KETO-ESTERS; ENANTIOSELECTIVE FLUORINATION; ARYLBORONIC ACIDS; ALPHA-AMINATION; ALDOL REACTION; MESO-EPOXIDES; COMPLEX; OXINDOLES; HYDROXYLATION; INTERMEDIATE;

D O I：

10.1021/ja908906n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly enantioselective catalytic asymmetric access to 3-aminooxindoles with a tetrasubstituted carbon stereocenter is described. 1-2 mol % of homobimetallic (R)-Ni-2-Schiff base 1 catalyzed the asymmetric amination of 3-substituted oxindoles with azodicarboxylates to give (R)-products in 99-89% yield and 99-87% ee. Reversal of enantiofacial selectivity was observed between bimetallic and monometallic Schiff base complexes, and monometallic (R)-Ni-Schiff base 2c gave (S)-products in 98-80% ee. Transformation of the products into an optically active oxindole with a spiro-beta-lactam unit and a known key intermediate for AG-041R synthesis is also described.

引用

页码：1255 / +

页数：5

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