Synthesis of optically active α-hydroxy ketones by enantioselective oxidation of silyl enol ethers with a fructose-derived dioxirane

被引：70

作者：

Adam, W ^{[1
]}

Fell, RT ^{[1
]}

Saha-Möller, CR ^{[1
]}

Zhao, CG ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 03期

关键词：

D O I：

10.1016/S0957-4166(98)00005-6

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 high enantioselectivities by the asymmetric oxidation of the silyl enol ethers 2 with in situ generated dioxirane from the fructose-derived ketone 1. Best results (ee values up to 82%) for this novel non-transition metal mediated asymmetric alpha-hydroxylation may be obtained, when an excess of the fructose-derived ketone 1 is employed at pH ca. 8 and short reaction times, Valuable mechanistic information on the spiro versus planar transition states for the oxygen-transfer process has been aquired through the absolute configuration of the resulting alpha-hydroxy ketone 3 products. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：397 / 401

页数：5

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