Open AccessManganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates
Author(s) -
Hannah Shenouda,
Erik J. Alexanian
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b03706
Subject(s) - chemistry , stereospecificity , alkyl , catalysis , manganese , hydroxymethyl , organic chemistry , primary (astronomy) , metal , carbon monoxide , combinatorial chemistry , physics , astronomy
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- d 2 alcohols. These studies use anionic metal carbonyl catalysis to access a synthetic equivalent of the challenging hydroxymethyl anion from carbon monoxide.