Enantioselective oxidation of vic-diols to optically active α-hydroxy ketones by a fructose-derived dioxirane

被引:27
作者
Adam, W [1 ]
Saha-Möller, CR [1 ]
Zhao, CG [1 ]
机构
[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany
关键词
D O I
10.1016/S0957-4166(98)00444-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Optically active alpha-hydroxy ketones 3 have been prepared in moderate to good enantioselectivities through asymmetrization of meso-, and kinetic resolution of, racemic vic-diols 2 by enantioselective oxidation with the in situ generated dioxirane from the fructose-derived ketone 1; the opposite sense in the enantioselectivity of the two processes is explained in terms of the hydrogen-bonded transition-state structures for the concerted C-H oxygen insertion. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4117 / 4122
页数:6
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