Catalytic enantioselective synthesis of oxindoles and benzofuranones that bear a quaternary stereocenter

被引：235

作者：

Hills, ID ^{[1
]}

Fu, GC ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 33期

关键词：

asymmetric synthesis; heterocycles; homogeneous catalysis; ion pairs; rearrangements;

D O I：

10.1002/anie.200351666

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A common feature in indole- and benzofuran-derived natural products is a quaternary stereocenter in the 3-position of the heterocycle. The catalyst (-) -1 promotes the asymmetric synthesis of such compounds 3 (with up to 99% ee) through the rearrangement of O-acylated benzofuranones (X = O) and oxindoles (X = NR2) 2.

引用

页码：3921 / 3924

页数：4

共 38 条

[21]

2-T

[22]

Li J., 2001, ANGEW CHEM, V113, P4906

[23] Gelsemine: A thought-provoking target for total synthesis [J].

Lin, H ;

Danishefsky, SJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) :36-51

[24] Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: Dual activation of the electrophile and the nucleophile [J].

Mermerian, AH ;

Fu, GC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) :4050-4051

[25] Studies towards the synthesis of diazonamide A. Unexpected formation of a 3,4-bridged indole [J].

Moody, CJ ;

Doyle, KJ ;

Elliott, MC ;

Mowlem, TJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (16) :2413-2419

[26]

Nicolaou K. C., 2003, ANGEW CHEM, V115, P1795

[27] The second total synthesis of diazonamide A [J].

Nicolaou, KC ;

Rao, PB ;

Hao, JL ;

Reddy, MV ;

Rassias, G ;

Huang, XH ;

Chen, DYK ;

Snyder, SA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (15) :1753-1758

[28]

Nicolaou KC, 2002, ANGEW CHEM INT EDIT, V41, P3495, DOI 10.1002/1521-3773(20020916)41:18<3495::AID-ANIE3495>3.0.CO

[29]

2-7

[30]

nicolaou kc, 2002, ANGEW CHEM, V114, P3645

← 1 2 3 4 →