Synlett 2020; 31(01): 60-64
DOI: 10.1055/s-0039-1690264
letter
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Addition of Alkynyl Esters and Ethers to Aldehydes Catalyzed by a Cyclopropyl Amino Alcohol Based Zinc Catalyst

Yun Zhou
a  Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China   Email: [email protected]
,
Lifeng Wang
a  Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China   Email: [email protected]
,
Shuoning Li
a  Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China   Email: [email protected]
,
Sijie Ma
a  Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China   Email: [email protected]
,
Patrick J. Walsh
b  Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104-6323, USA
,
Qinghua Bian
a  Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China   Email: [email protected]
,
Fengqi Li
c  Institute of Plant and Environment Protection, Beijing Academy of Agriculture and Forestry Sciences, No. 9 Shuguang Garden, Central Road, Beijing, 100097, P. R. of China   Email: [email protected]
,
Min Wang
a  Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China   Email: [email protected]
,
Jiangchun Zhong
a  Department of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China   Email: [email protected]
› Author Affiliations
We are grateful to the National Key Technology Research and Development Program of China for financial support (No. 2017YFD0201404).
Further Information

Publication History

Received: 28 August 2019

Accepted after revision: 22 October 2019

Publication Date:
03 December 2019 (online)


Abstract

A novel and highly enantioselective synthesis of hydroxyalkynyl esters and ethers through the asymmetric addition of alkynyl esters or ethers to aldehydes promoted by a cyclopropyl amino alcohol based zinc catalyst has been developed. The method afforded a library of new enantioenriched hydroxyalkynol esters and ethers (up to 93% yield; 95% ee), and it was compatible with a broad range of functional groups. Moreover, it could be used in the synthesis of carbon-chain-elongated enantioenriched hydroxyalkynol esters and (2R,5R)-musclide-A1, a cardiotonic potentiating principle from musk.

Supporting Information

 
  • References and Notes

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