Synlett 2019; 30(02): 240-244
DOI: 10.1055/s-0037-1611363
letter
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols by Vinylogous Aldol Reaction of 3-Methylcyclohex-2-en-1-one with (Het)aryl Trifluoromethyl Ketones

Fenfen Chen ◊
a   Zhejiang Provincial Key Laboratory for Chemical and Biological Processing Technology of Farm Products, School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, P. R. of China   Email: chemhanxy@zust.edu.cn
,
Zhixin Chang ◊
a   Zhejiang Provincial Key Laboratory for Chemical and Biological Processing Technology of Farm Products, School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, P. R. of China   Email: chemhanxy@zust.edu.cn
,
Chigumbu Paidamoyo
a   Zhejiang Provincial Key Laboratory for Chemical and Biological Processing Technology of Farm Products, School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, P. R. of China   Email: chemhanxy@zust.edu.cn
,
Xiaofei Zeng
b   College of Materials, Chemistry, and Chemical Engineering, Hangzhou Normal University, Hangzhou 310036, P. R. of China
,
Yongjiang Wang
a   Zhejiang Provincial Key Laboratory for Chemical and Biological Processing Technology of Farm Products, School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, P. R. of China   Email: chemhanxy@zust.edu.cn
,
Xiaoyu Han*
a   Zhejiang Provincial Key Laboratory for Chemical and Biological Processing Technology of Farm Products, School of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, P. R. of China   Email: chemhanxy@zust.edu.cn
› Author Affiliations
We acknowledge the Natural Science Foundation of Zhejiang Province (LY17B020003), Qiangjiang Talents Plan of Zhejiang Province (QJD1602024) and Zhejiang University of Science & Technology (F702103H06) for generous financial support.
Further Information

Publication History

Received: 02.10.20218

Accepted after revision: 09 November 2018

Publication Date:
10 December 2018 (online)


These authors contributed equally to this work.

Abstract

A direct enantioselective vinylogous aldol reaction of trifluoromethyl ketones with 3-methylcyclohex-2-en-1-one through hydrogen-bond-directing dienamine catalysis by a diamine–sulfonamide catalyst has been demonstrated. A range of trifluoromethylated tertiary alcohols were efficiently produced in yields of up to 86% and with 93% enantioselectivity.

Supporting Information

 
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