Observations on selectivity reversal during chiral auxiliary-directed asymmetric nucleophile additions to arene–manganese tricarbonyl complexes

Abstract

A study of hydride nucleophile reactions with η⁶-(2R, 5R)-dimethylpyrrolidinylbenzene–manganese tricarbonyl hexafluorophosphate 1 reveals an unexpected reversal of selectivity during addition of hydride to the diastereotopic meta carbons, which is explained on the basis of changes in transition state location as the reactivity of the nucleophile is varied.