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有机催化对映选择性芳基酮与杂芳基三氟甲基酮水合物的交叉缩醛反应,用于合成α-三氟甲基叔醇。

Organocatalytic enantioselective cross-aldol reaction of aryl ketones with heteroaromatic trifluoromethyl ketone hydrates for the synthesis of α-trifluoromethyl tertiary alcohols.

机构信息

Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, P. R. China.

出版信息

Org Biomol Chem. 2023 Jun 28;21(25):5234-5239. doi: 10.1039/d3ob00619k.

DOI:10.1039/d3ob00619k
PMID:37293869
Abstract

An efficient organocatalytic enantioselective cross-aldol reaction of aryl ketones with heteroaromatic trifluoromethyl ketone hydrates enolate intermediates has been developed. The cross-aldol reactions catalyzed by Takemoto-type thiourea catalysts proceeded well under mild conditions, furnishing a variety of enantioenriched α-trifluoromethyl tertiary alcohols bearing N-heteroaromatics with good to high yields and enantioselectivities. This protocol features broad substrate scope, good functional group tolerance, and easy gram-scale preparation.

摘要

一种高效的手性有机催化芳基酮与杂芳基三氟甲基酮水合烯醇化物中间体的对映选择性交叉羟醛反应已经被开发出来。Takemoto 型硫脲催化剂催化的交叉羟醛反应在温和条件下进行得很好,提供了多种具有 N-杂芳基的对映体富集的α-三氟甲基叔醇,产率和对映选择性好到高。该方案具有广泛的底物范围、良好的官能团耐受性和易于进行克级制备。

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