Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 14, Pages 5104-5106Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo900710e
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Funding
- National Natural Science Foundation of China [20732005]
- State Basic and Development Research Program [2006CB806105]
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The sequential treatment of optically active terminal propargylic alcohols with n-BuLi/(HCHO)(n) and regioselective chlorination afforded the corresponding optically active 4-chloro-2-butyn-1-ols. With R-1 being a methyl or an ethyl group, an alternative for the synthesis of the corresponding optically active propargylic alcohols is the Novozym 435-catalyzed kinetic resolution of these racemic 4-chloro-2-butyn-1-ols. The subsequent reaction of these optically active 4-chloro-2-butyn-1-ols, with the corresponding Grignard reagents under the catalysis of 5 mol % of CuCN afforded the optically active secondary 2,3-allenols in good yields with up to >99% ee.
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