A novel highly stereoselective synthesis of chiral 5-and 4,5-substituted 2-oxazolidinones

被引:38
作者
Bertau, M [1 ]
Bürli, M
Hungerbühler, E
Wagner, P
机构
[1] Tech Univ Dresden, Inst Biochem, D-01062 Dresden, Germany
[2] Rohner AG, CH-4133 Pratteln, Switzerland
[3] Basel Inst Appl Sci, CH-4132 Muttenz, Switzerland
关键词
D O I
10.1016/S0957-4166(01)00364-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A novel highly stereoselective synthesis of chiral mono- and bicyclic 4- and 4,5-substituted 2-oxazolidinones starting from P-keto esters was developed. After bioreduction with S. cerevisiae the resulting homochiral P-hydroxy esters are transformed into their hydrazides. Treatment with NaNO2/H+ then furnishes 2-oxazolidinones in high e.e. (similar to 99%) and d.e. (> 99%). The ring formation proceeds via a highly concerted sextet rearrangement with full retention of configuration at the stereocentres. Enantiopure 1,2-amino alcohols can subsequently be obtained by saponification of the 2-oxazolidinone products. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2103 / 2107
页数:5
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