| Literature DB >> 21894954 |
Douglas T Genna1, Gary H Posner.
Abstract
Carboxylic acids were converted directly in 56-99% yields into methyl, n-butyl, and isopropyl ketones using excess cyanocuprates R(2)CuLi·LiCN. A substrate with a stereocenter α to the carboxylic acid was converted into ketones with very little loss of enantiomeric purity. A variety of functional groups were tolerated including aryl bromides. This direct transformation of a carboxylic acid into ketone with minimal tertiary alcohol formation is proposed to involve a relatively stable copper ketal tetrahedral intermediate.Entities:
Year: 2011 PMID: 21894954 DOI: 10.1021/ol202237j
Source DB: PubMed Journal: Org Lett ISSN: 1523-7052 Impact factor: 6.005