Synlett 2014; 25(6): 809-812
DOI: 10.1055/s-0033-1340824
letter
© Georg Thieme Verlag Stuttgart · New York

Access to Chiral Tertiary α-Hydroxy-β-Ynyl Esters via One-Pot Addition and Kinetic Resolution

Hong-Bin Chen*
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China   eMail: hbchan@xmu.edu.cn
,
Wen-Han Lai
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China   eMail: hbchan@xmu.edu.cn
,
Yan Zhao
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China   eMail: hbchan@xmu.edu.cn
,
Dan-Dan Qin
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China   eMail: hbchan@xmu.edu.cn
,
Yuan-Ping Ruan
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China   eMail: hbchan@xmu.edu.cn
,
Zhao-Hui Zhou
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China   eMail: hbchan@xmu.edu.cn
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Publikationsverlauf

Received: 26. Dezember 2013

Accepted after revision: 22. Januar 2014

Publikationsdatum:
13. Februar 2014 (online)


Abstract

Chiral amino alcohol promoted one-pot addition of zinc alkynylides to α-keto esters and kinetic resolution of the resulting tertiary propargylic alcohols was developed. The reaction provided us an alternative approach to access optically active tertiary α-hydroxy-β-ynyl esters with enantiomeric excesses up to 98%.

Supporting Information