Highly stereoselective kinetic resolution of α-allenic alcohols: an enzymatic approach

• DOI: 10.1016/j.tetlet.2015.12.098
• Publication Date: 2015-12-25T01:17:07Z
• Authors: Wenhua Li; Zuming Lin; Long Chen; Xuechao Tian; Yan Wang; Sha-Hua Huang; Ran Hong
• Keywords: 01 natural sciences; 0104 chemical sciences

A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones–Burgess empirical model was modified to interpret the reversed selectivity during the acetylation of secondary alcohol. The methyl group at C(2) of allenic alcohols implied a small structural adjustment in the catalytic triad of lipase AK, representing a potential direction for future site-directed mutagenesis.