Enzyme-catalysed asymmetric synthesis of a spiro[3.3]heptane derivative with axial chirality and enzymatic resolution of racemic spiro[3.3]heptane derivatives

Abstract

2,6-Bis(acetoxymethyl)-2,6-bis(hydroxymethyl)spiro[3.3]heptane with axial chirality and moderate optical purity has been prepared in high chemical yield by pig liver esterase-catalysed asymmetric hydrolysis of 2,2,6,6-tetrakis (acetoxymethyl)spiro[3.3]heptane. Similarly, racemic 2,6-disubstituted spiro[3.3] heptane derivatives with axial chirality were resolved by enantioselective enzyme-catalysed hydrolysis.