Synthesis of optically active indane building blocks using an enzymatic resolution approach

Abstract

A highly efficient synthesis of indane building blocks is described. First, enantioenriched diastereomerically pure 2- and 3-substituted methyl indane alcohols were synthesized using an enzymatic resolution reaction with Amano PS (Burkholderia cepacia lipase) and Novozym 435 (Candida antarctica lipase B). Then, obtained cis-alcohols were converted into trans-alcohols using the Mitsunobu reaction with para-nitrobenzoic acid. The Mitsunobu reaction with DPPA was used to obtain azides that were reduced to the corresponding target amines without decreasing ee values. This work expands known approaches to synthesizing indane building blocks and provides an efficient protocol for obtaining optically active alcohols and amines.