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Short Paper | Special issue | Vol 97, No. 1, 2018, pp.604-611
Published online, 18th May, 2018
DOI: 10.3987/COM-18-S(T)45
Preparation of Optically Active 2,2-Disubstituted 5-Hydroxychromenes by the Enzymatic Resolution of Racemic Esters

Mika Kainuma, Ai Yamada, Kazuaki Katakawa, and Takuya Kumamoto*

*Department of Synthetic Organic Chemistry, School of Pharmaceutical Sciences, Hiroshima University, 1-2-3 Kasumi, Minami-ku, Hiroshima 734-8551, Japan


Enzymatic kinetic resolution of racemic esters of 2,2-disubstituted 5-hydroxychromenes was examined. Transesterification of acetate using Amano Lipase PS in the presence of t-BuOH was most effective to give the corresponding optically active acetate in 18% yield and 95% ee. The absolute configuration of the acetate was determined as R based on the conversion to teretifolione B with natural absolute configuration.