Abstract
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.
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