Organocatalytic Kinetic Resolution of Propargylic Alcohols

V. B. Birman; L. Guo

doi:10.1055/s-2006-955557

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Synfacts 2006(12): 1283-1283
DOI: 10.1055/s-2006-955557

Organo- and Biocatalysis

Organocatalytic Kinetic Resolution of Propargylic Alcohols

Contributor(s): Benjamin List, Daniela Kampen
V. B. Birman*, L. Guo
Washington University, St. Louis, USA

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Publication History

Publication Date:
22 November 2006 (online)

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Significance

A Lewis base catalyzed kinetic resolution of propargylic alcohols has been developed. Acylation of racemic secondary alcohols 1 in the presence of propionic anhydride and 4 mol% of chiral benzotetramisole (BTM) 2 provides enantioenriched products of type 3 and 4 with selectivity factors of up to 32. Linear and branched alkyl substrates as well as aryl precursors can be used.