An Organocatalytic Asymmetric Nazarov Cyclization

被引：103

作者：

Basak, Ashok K. ^{[1
]}

Shimada, Naoyuki ^{[1
]}

Bow, William F. ^{[1
]}

Vicic, David A. ^{[1
]}

Tius, Marcus A. ^{[1
,2
]}

机构：

[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA

[2] Canc Res Ctr Hawaii, Honolulu, HI 96813 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 24期

基金：

美国国家卫生研究院;

关键词：

DIRECT CONJUGATE ADDITION; AMINE-THIOUREA CATALYST; QUATERNARY STEREOCENTERS; ALPHA-DIKETONES; BOND DONORS; CONSTRUCTION; NITROALKENES; ACIDS;

D O I：

10.1021/ja103028r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An organocatalytic asymmetric Nazarov cyclization of diketoesters that proceeds by means of a dual activation mechanism has been developed. Screening of a number of catalysts led to a new thiourea that incorporates a primary amino group. The method gives rise to cyclic products with two adjacent quaternary asymmetric carbon atoms, one of which is an all-carbon stereocenter, with complete or nearly complete diastereoselectivity and in high or very high enantiomeric excess. A brief and very convenient synthesis of the acyclic diketoester starting materials through nucleophilic addition to a ketene is also described.

引用

页码：8266 / +

页数：3

共 43 条

[1] Stereoselective synthesis of acetoacetate-derived enol triflates [J].