Highly enantioselective synthesis of α-trichloromethyldihydropyrans catalyzed by bifunctional organocatalysts

被引：23
|
作者：
Wang, Hai-Feng [1 ]
Li, Peng [1 ]
Cui, Hai-Feng [1 ]
Wang, Xiao-Wei [1 ]
Zhang, Jun-Kang [1 ]
Liu, Wen [2 ]
Zhao, Gang [1 ,2 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
来源：
TETRAHEDRON | 2011年 / 67卷 / 10期
基金：
中国国家自然科学基金;
关键词：
Michael addition; Enantioselectivity; Trichloromethyl ketones; Dihydropyrans; Bifunctional organocatalysts; RING-CLOSING METATHESIS; CYCLIC 1,3-DICARBONYL COMPOUNDS; ASYMMETRIC CONJUGATE ADDITIONS; TERTIARY AMINE CATALYSTS; STEREOSELECTIVE-SYNTHESIS; MICHAEL REACTIONS; VINYL ETHERS; KETO ESTERS; DIHYDROPYRANS; DERIVATIVES;
D O I：
10.1016/j.tet.2011.01.043
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective Michael addition of alpha-cyanoketones to alpha,beta-unsaturated trichloromethyl ketones was firstly reported. With a phenylalanine-derived bifunctional piperazine/thiourea catalyst, a series of alpha-trichloromethyldihydropyrans were obtained with up to 95% ee and 99% yield. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1774 / 1780
页数：7
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