Lipase-catalysed asymmetric and enantioselective esterification of spiro[3.3]heptanes in organic solvents

Abstract

Lipase-catalysed asymmetric esterification of 2,2,6,6-tetrakis(hydroxymethyl)spiro[3.3]heptane in both isopropyl ether and pyridine gave regiospecifically 2,6-bis(acetoxymethyl)-2,6-bis(hydroxymethyl)spiro[3.3]heptane having axial chirality and moderate optical purity. Similarly, racemic diols of spiro compounds having axial chirality were resolved by lipase-catalysed enantioselective esterification in isopropyl ether.