Enantioselective synthesis of α-bromo acid derivatives and bromohydrins from tartrate derived bromoacetals

SA Boyes, AT Hewson

Index: Boyes, Scott A.; Hewson, Alan T. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 16 p. 2759 - 2765

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Abstract

Bromination of the acetals 4 derived from aryl alkyl ketones, ArCOR, and (2R, 3R)-tartaric acid results in bromoacetals 5 with 78–90% de. Hydrolysis of those compounds with Ar= 4- methoxyphenyl or 3-bromo-4-methoxyphenyl results, after recrystallisation, in α- bromoketones 8 with 66–98% ee which are shown to undergo the Baeyer–Villiger oxidation to α-bromoesters 9 with minimal racemisation. α-Bromoketone 8d is shown to undergo ...