Enantioselective Bromocycloetherification by Lewis Base/Chiral Bronsted Acid Cooperative Catalysis

被引：181
|
作者：
Denmark, Scott E. [1 ]
Burk, Matthew T. [1 ]
机构：
[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 01期
基金：
美国国家卫生研究院;
关键词：
ASYMMETRIC BROMOLACTONIZATION; TETRAHYDROPYRAN SYSTEMS; EPOXIDE OPENINGS; ACTIVATION; OLEFINS; STRATEGIES; ALKENES; RING; BOND;
D O I：
10.1021/ol203033k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A binary catalyst system for the enantioselective bromocycloetherification of 5-arylpentenois is described. The combination of an achiral Lewis base and a chiral Bronsted acid affords good enantioselectivities for the cyclization of Z configured 5-arylpentenois to form bromomethyltetrahydrofurans. The constitutional site selectivity is highly dependent upon the aromatic substituent and the configuration of the double bond.
引用
收藏
页码：256 / 259
页数：4
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