Memory of chirality in rebound cyclizations of alpha-amide radicals

作者：Sasmal Aniruddha; Taniguchi Tsuyoshi; Wipf Peter; Curran Dennis P^*

来源：Canadian Journal of Chemistry, 2013, 91(1): 1-5.

DOI：10.1139/v2012-085

• memory of chirality
• radical reactions
• amides
• stereochemistry

Reduction of (S)-N-(2-bromoallyl)-N-(tert-butyl)-2-methyl-3-phenylpropanamide with tributyltin hydride provides (3S,4S)-3-benzyl-1-(tert-butyl)-3,4-dimethylpyrrolidin-2-one with about 80% retention of chirality at the stereocenter adjacent to the amide carbonyl group. This memory of chirality is suggested to occur by transfer of chirality from a stereocenter to an axis, then from the axis back to a new stereocenter.

• 出版日期2013-1