Synlett 2019; 30(07): 860-862
DOI: 10.1055/s-0037-1611759
letter
© Georg Thieme Verlag Stuttgart · New York

A Concise Enantioselective Synthesis of (S)-Preclamol via Asymmetric Catalytic Negishi Cross-Coupling Reaction

Yun Zhou
,
Chunxiao Liu
,
Lifeng Wang
,
Leng Han
,
Shicong Hou
,
Qinghua Bian
,
Jiangchun Zhong*
Department of Applied Chemistry,China Agricultural University2, West Yuanmingyuan Road, Beijing 100193, P. R. of China   Email: zhong@cau.edu.cn
› Author Affiliations
We are thankful to the National Key Technology Research and Development Program of China (No. 2017YFD0201404) for the financial support.
Further Information

Publication History

Received: 21 February 2019

Accepted after revision: 21 February 2019

Publication Date:
26 March 2019 (online)

These authors contributed equally to this work and should be considered as co-first authors

Abstract

A novel, concise, and efficient enantioselective synthesis of (S)-preclamol (87% ee, 51% total yield) has been developed. The key steps of this synthetic approach included cobalt-catalyzed asymmetric catalytic cross-coupling of α-bromo ester with arylzinc and the reduction of chiral ester to diol with a tertiary carbon atom. Moreover, it was demonstrated that our enantioselective Negishi cross-coupling was a powerful tool to construct stereogenic benzylmethyl center in chiral drugs on a gram scale.

Supporting Information

 
  • References and Notes

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