Enantioselective Cleavage of meso-Nitrodiol Diacetates by an Esterase Concentrate from Fresh Pig Liver: Preparation of Useful Nitroaliphatic Building Blocks for EPC Syntheses

Abstract

Diacetates of meso-2-nitro-1,3-diols, readily available from nitroalkanes and aldehydes, are saponified to crystalline monoacetates of > 97% ee by pig liver esterase (PLE). A general discussion of this type of EPC synthesis (EPC: enantiomerically pure compounds) is given, and a specific example is described in detail: a procedure for the preparation of a very inexpensive PLE concentrate and of a PLE solution from fresh liver, and a procedure for preparing 20 g amounts of enantiomerically pure (1S, 2S, 3R)-3-hydroxy-2-nitro-cyclohexyl acetate.