A convenient preparation of 3,3,3-trifluoro-1-propynylamines and their Lewis acid catalyzed reaction with carbonyl compounds leading to (Z)-α-(trifluoromethyl)-α,β-unsaturated amides

被引:16
作者
Mantani, T [1 ]
Shiomi, K [1 ]
Konno, T [1 ]
Ishihara, T [1 ]
Yamanaka, H [1 ]
机构
[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan
关键词
D O I
10.1021/jo001760v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N,N-Dialkyl(3,3,3-trifluoro-1-propynyl)amines were readily prepared by a three-step procedure starting from commercially available 2,2,3,3,3 -pentafluoropropanol. These fluorinated alkynylamines reacted smoothly with a variety of aldehydes or ketones in the presence of a catalytic amount of Lewis acid and;molecular sieves 4 Angstrom at ambient temperature to produce the corresponding alpha-(trifluoromethyl)-alpha,beta -unsaturated amides in good to excellent yields with high Z-stereoselectivity.
引用
收藏
页码:3442 / 3448
页数:7
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