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Manganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates.

ABSTRACT: The development of a stereospecific hydroxymethylation of alkyl tosylates using an inexpensive, first-row catalyst is described. The transformation proceeds under mild conditions with low pressure to deliver homologated alcohols as products. Chiral, nonracemic ?-branched primary alcohols are obtained with high enantiospecificity from easily accessed secondary alkyl substrates. Simple modification of the reaction system also permits access to ?-d2 alcohols. These studies use anionic metal carbonyl catalysis to access a synthetic equivalent of the challenging hydroxymethyl anion from carbon monoxide.

SUBMITTER: Shenouda H

PROVIDER: S-EPMC7147876 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Manganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates.

Shenouda Hannah H Alexanian Erik J EJ

Organic letters 20191105 22

The development of a stereospecific hydroxymethylation of alkyl tosylates using an inexpensive, first-row catalyst is described. The transformation proceeds under mild conditions with low pressure to deliver homologated alcohols as products. Chiral, nonracemic β-branched primary alcohols are obtained with high enantiospecificity from easily accessed secondary alkyl substrates. Simple modification of the reaction system also permits access to α-d2 alcohols. These studies use ani ...[more]

PMID: 31689117

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