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

Yun Zhou; Lifeng Wang; Shuoning Li; Sijie Ma; Patrick J. Walsh; Qinghua Bian; Fengqi Li; Min Wang; Jiangchun Zhong

doi:10.1055/s-0039-1690264

Synlett, Inhaltsverzeichnis

Synlett 2020; 31(01): 60-64
DOI: 10.1055/s-0039-1690264

letter

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

Yun Zhou

^aDepartment of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China eMail: zhong@cau.edu.cn

,

Lifeng Wang

^aDepartment of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China eMail: zhong@cau.edu.cn

,

Shuoning Li

^aDepartment of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China eMail: zhong@cau.edu.cn

,

Sijie Ma

^aDepartment of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China eMail: zhong@cau.edu.cn

,

Patrick J. Walsh

^bRoy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104-6323, USA

,

Qinghua Bian

^aDepartment of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China eMail: zhong@cau.edu.cn

,

Fengqi Li∗

^cInstitute 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: pandit@163.com

,

Min Wang

^aDepartment of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China eMail: zhong@cau.edu.cn

,

Jiangchun Zhong∗

^aDepartment of Applied Chemistry, China Agricultural University, 2 West Yuanmingyuan Road, Beijing 100193, P. R. of China eMail: zhong@cau.edu.cn

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Abstract

Alle Artikel dieser Rubrik

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.

Key words

zinc catalysis - hydroxyalkynyl esters - hydroxyalkynyl ethers - alkynylation - musclide-A1 - asymmetric catalysis

Volltext

Referenzen

References and Notes

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