General CuBr2-catalyzed highly enantioselective approach for optically active allenols from terminal alkynols

Xin Huang; Tao Cao; Yulin Han; Xingguo Jiang; Weilong Lin; Jiasheng Zhang; Shengming Ma

doi:10.1039/C5CC00697J

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General CuBr₂-catalyzed highly enantioselective approach for optically active allenols from terminal alkynols†

Xin Huang,^a Tao Cao,‡^b Yulin Han,‡^b Xingguo Jiang,‡^b Weilong Lin,‡^b Jiasheng Zhang ‡^b and Shengming Ma*^ab

Author affiliations

* Corresponding authors

^a Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, People's Republic of China

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China
E-mail: masm@sioc.ac.cn

Abstract

Here, we show a CuBr₂-catalyzed approach for a highly enantioselective synthesis (93–99% ee) of allenols from aldehydes and terminal alkynols with the absolute configuration being controlled by applying readily available (R)- or (S)-α,α-diphenylprolinol.

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Article information

DOI: https://doi.org/10.1039/C5CC00697J
Article type: Communication
Submitted: 24 Jan 2015
Accepted: 05 Mar 2015
First published: 06 Mar 2015

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Chem. Commun., 2015,51, 6956-6959

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General CuBr₂-catalyzed highly enantioselective approach for optically active allenols from terminal alkynols

X. Huang, T. Cao, Y. Han, X. Jiang, W. Lin, J. Zhang and S. Ma, Chem. Commun., 2015, 51, 6956 DOI: 10.1039/C5CC00697J

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