306972-70-3Relevant academic research and scientific papers
Enantioselective synthesis of α-bromo acid derivatives and bromohydrins from tartrate derived bromoacetals
Boyes, Scott A.,Hewson, Alan T.
, p. 2759 - 2765 (2007/10/03)
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 carbonyl reduction to threo-bromohydrin 15 with retention of stereochemistry.
