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使用新型双功能哌嗪-硫脲催化剂高对映选择性和非对映选择性合成α-三氟甲基二氢吡喃。

Highly enantio- and diastereoselective synthesis of alpha-trifluoromethyldihydropyrans using a novel bifunctional piperazine-thiourea catalyst.

机构信息

Key Laboratory of Organofluorine Chemistry and Key Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.

出版信息

Chem Commun (Camb). 2009 Dec 21(47):7369-71. doi: 10.1039/b915210e. Epub 2009 Oct 22.

Abstract

The first enantioselective Michael addition of alpha-cyanoketones to alpha,beta-unsaturated trifluoromethyl ketones using a novel piperazine-thiourea catalyst was described. The resulting alpha-trifluoromethyldihydropyrans were obtained in high yields and with up to 95% ee within a short reaction time. A useful transformation of the chiral adduct was also illustrated.

摘要

描述了使用新型哌嗪-硫脲催化剂进行的α-氰基酮对α,β-不饱和三氟甲基酮的首例对映选择性迈克尔加成反应。在短反应时间内,以高收率和高达 95%的对映选择性得到了α-三氟甲基二氢吡喃。还说明了手性加成物的一种有用转化。

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