biostudies-literatureShenouda HNational Institute of General Medical SciencesNIGMS NIH HHS9268-9271https://www.ebi.ac.uk/biostudies/studies/S-EPMC7147876biostudies-literatureUnknown21(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 anionic metal carbonyl catalysis to access a synthetic equivalent of the challenging hydroxymethyl anion from carbon monoxide.Organic lettersManganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates.PMC7147876R35 GM118055R35 GM131708Shenouda HAlexanian EJfalseManganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates.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 anionic metal carbonyl catalysis to access a synthetic equivalent of the challenging hydroxymethyl anion from carbon monoxide.2019-01-01T00:00:00Z2019 Nov2025-04-26T14:39:34.311Z2020-11-19T15:26:23ZS-EPMC71478763168911710.1021/acs.orglett.9b03706