The development of a stereospecific, manganese-catalyzed, hydroxymethylation of unactivated alkyl tosylates is described. The mild, low pressure reaction proceeds with near-complete inversion of the stereocenter to give β-branched, primary alcohols, and can be used to obtain α-deuterated products. This umpolung transformation constitutes a unique approach to the one carbon extension of alcohols from easily accessed chiral, non-racemic starting materials.

Stereospecific, manganese-catalyzed hydroxymethylation of unactivated alkyl tosylates

2019 Fall National Meeting

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