Organocatalytic Direct Asymmetric Aldol Reactions of 3-Isothiocyanato Oxindoles to Ketones: Stereocontrolled Synthesis of Spirooxindoles Bearing Highly Congested Contiguous Tetrasubstituted Stereocenters

被引：190

作者：

Chen, Wen-Bing ^{[1
,3
]}

Wu, Zhi-Jun ^{[2
]}

Hu, Jing ^{[1
]}

Cun, Lin-Feng ^{[1
]}

Zhang, Xiao-Mei ^{[1
]}

Yuan, Wei-Cheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Peoples R China

[2] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Peoples R China

[3] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 09期

基金：

中国国家自然科学基金;

关键词：

CATALYTIC ENANTIOSELECTIVE SYNTHESIS; ALPHA-ISOTHIOCYANATO IMIDES; QUATERNARY STEREOCENTERS; CRUCIFEROUS PHYTOALEXIN; ENANTIOMERIC ENRICHMENT; STRESS METABOLITES; TERTIARY ALCOHOLS; ACID-DERIVATIVES; ALLENIC ESTERS; AMINO-ACIDS;

D O I：

10.1021/ol200724q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first example of a direct catalytic asymmetric intermolecular aldol reaction of 3-isothiocyanato oxindoles to simple ketones with bifunctional thiourea-tertiary amine as catalyst is reported. This strategy provides a promising approach for the asymmetric synthesis of a range of enantioenriched spirocyclic oxindoles bearing two highly congested contiguous tetrasubstituted carbon stereocenters. Versatile transformations of the spirocyclic oxindole products into other structurally diverse spirocyclic oxindoles have also been demonstrated.

引用

页码：2472 / 2475

页数：4

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