Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C-3 Position

被引：1225

作者：

Zhou, Feng ^{[1
]}

Liu, Yun-Lin ^{[1
]}

Zhou, Jian ^{[1
]}

机构：

[1] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 09期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; bioactive compounds; oxindole framework; stereoselectivity; tetrasubstituted carbon stereocenters; QUATERNARY CARBON CENTERS; ENANTIOSELECTIVE SYNTHESIS; ALPHA-ARYLATION; ALDOL REACTION; 3,3-DISUBSTITUTED OXINDOLES; PROCHIRAL NUCLEOPHILES; ALLYLIC ALKYLATION; CARBENE LIGANDS; CONSTRUCTION; ISATINS;

D O I：

10.1002/adsc.201000161

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The 3,3 '-disubstituted oxindole structural motif is a prominent feature in many alkaloid natural products, which include all kinds of tetrasubstituted carbon stereocenters, spirocyclic or not, all-carbon or heteroatom-containing. The catalytic asymmetric synthesis of the tetrasubstituted carbon stereocenter at the C-3 position of the oxindole framework integrates new synthetic methods and chiral catalysts, reflects the latest achievements in asymmetric catalysis, and facilitates the synthesis of sufficient quantities of related compounds as potential medicinal agents and biological probes. This review summarizes the recent progress in this area, and applications in the total synthesis of related bioactive compounds.

引用

页码：1381 / 1407

页数：27

共 135 条

[1] Asymmetric construction of quaternary carbon stereocenters: High stereoselection in Mukaiyama aldol reactions of 2-siloxyindoles with chiral aldehydes [J].