Chemo-enzymatic preparation of hydroxymethyl ketones

Article abstract of DOI:10.1039/b206851f

A series of hydroxymethyl ketones 4a-g were obtained from the corresponding halogenomethyl ketones 2a-g via 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.