Catalytic Asymmetric α-Alkylation of Ketones and Aldehydes with N-Benzylic Sulfonamides through Carbon-Nitrogen Bond Cleavage

被引：43
|
作者：
Weng, Zhen-Tao [1 ]
Li, Yuan [1 ]
Tian, Shi-Kai [1 ]
机构：
[1] Univ Sci & Technol, Dept Chem, Joint Lab Green Synthet Chem, Hefei 230026, Anhui, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 19期
基金：
中国国家自然科学基金;
关键词：
FRIEDEL-CRAFTS REACTION; S(N)1-TYPE REACTION; CYCLIC-KETONES; NUCLEOPHILES; DERIVATIVES; ACIDS;
D O I：
10.1021/jo2014142
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A range of ketones and aldehydes smoothly undergo asymmetric S(N)1 alpha-alkylation with N-benzylic sulfonamides in the presence of 10 mol % of a chiral imidazolidinone and trifluoroacetic acid to give the corresponding products in good to excellent yields and with good enantioselectivity. This chemistry has been successfully extended to the asymmetric desymmetrization of 4-substituted cyclohexanones, which exhibits greater than 99:1 diastereoselectivity and good enantioselectivity.
引用
收藏
页码：8095 / 8099
页数：5
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