Enantioselective Synthesis of Axially Chiral Tetrasubstituted Allenes via Lipase-Catalyzed Desymmetrization

Abstract

Lipase from Pseudomonas fluorescens efficiently catalyzes the transesterification of prochiral tetrasubstituted allenic diols yielding highly enantioenriched axially chiral allenyl monoesters. In combination with subsequent 5-endo-trig cyclizations geminally disubstituted dihydrofurans are accessible in high optical purity.

Key words

allenes - axial chirality - desymmetrization - biocatalysis - 5-endo-trig cyclization

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