Enzymatic desymmetrization of 2-amino-2-methyl-1,3-propanediol: asymmetric synthesis of (S)-N-Boc-N,O-isopropylidene-alpha-methyl-serinal and (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one

摘要

We report herein, the novel enzymatic desymmetrization of 2-tert-butoxycarbonylamino-2-methyl-1,3-propanediol 1. This method makes it possible to prepare (S)-N-Boc-N,O-isopropylidene-alpha-methylserinal 3, which is a chiral building block for the synthesis of a variety of a-substituted alanine derivatives. Moreover, optically active (4R)-methyl-4-[2-(thiophen-2-yl)ethyl]oxazolidin-2-one 4. one of the key intermediates in the synthesis of a novel immunosuppressant, has been prepared by this methodology. (c) 2005 Elsevier Ltd. All rights reserved.