β-Hydroxypiperidinecarboxylates: additions to the chiral pool from bakers' yeast reductions of β-ketopiperidinecarboxylates

DW Knight, N Lewis, AC Share, D Haigh

Index: Knight, David W.; Lewis, Neil; Share, Andrew C.; Haigh, David Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 22 p. 3673 - 3683

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Citation Number: 26

Abstract

Reduction of the piperidine keto esters 16–19 using fermenting bakers' yeast provides high yields of the corresponding hydroxy esters 20, 26, 32 and 37 respectively, exclusively as the cis-diastereoisomers and with good levels (80%) of enantiomeric enrichment. The relative stereochemistries of the products were deduced from NMR data while the absolute configurations were determined by degradation to known piperidinemethanol derivatives ...