Chemo-enzymatic preparation of hydroxymethyl ketones

C Paizs, M Toşa, C Majdik, V Bódai, L Novák…

Index: Paizs, Csaba; Tosa, Monica; Majdik, Cornelia; Bodai, Viktoria; Novak, Lajos; Irimie, Florin-Dan; Poppe, Laszlo Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 21 p. 2400 - 2402

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Citation Number: 7

Abstract

A series of hydroxymethyl ketones 4a–g were obtained from the corresponding halogenomethyl ketones 2a–gvia their transformation into acetoxymethyl ketones 3a–g by 18-crown-6 catalysed substitution with NaOAc followed by Novozyme 435™ catalysed ethanolysis. This convenient chemo-enzymatic route provides a mild, heavy-metal-free alternative to the direct α-hydroxylations of methyl ketones 1a–g.