Enantioselective Synthesis of Cyclohexenol Derivatives from γ-Aryl-Substituted Enals via an Organocatalyzed Three-Component Reaction

被引：11
|
作者：
Majee, Debashis [1 ]
Jakkampudi, Satish [1 ]
Arman, Hadi D. [1 ]
Zhao, John C. -G. [1 ]
机构：
[1] Univ Texas San Antonio, Dept Chem, One UTSA Circle, San Antonio, TX 78249 USA
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 22期
基金：
美国国家科学基金会;
关键词：
MANNICH REACTION; ALDOL REACTION; CYCLOADDITION; ALKYLATION; ACTIVATION; CATALYSIS; ALDEHYDES;
D O I：
10.1021/acs.orglett.9b03532
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A three-component reaction between gamma-aryl-substituted alpha,beta-unsaturated aldehydes and nitroalkenes was realized by using cinchona alkaloid-derived (thio)ureas and squaramides via the dienolate intermediates. This unprecedented 1,3- and 1,5-reactivity of dienolates of the gamma-aryl-alpha,beta-unsaturated aldehydes led to the formation of cyclohexenol derivatives with four contiguous stereogenic centers and a chiral substituent at C2 with good diastereoselectivities and high ee values. Such reactivities of the dienolates are totally different from those of the corresponding dienamine intermediates.
引用
收藏
页码：9166 / 9170
页数：5
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