Ontology highlight
ABSTRACT:
SUBMITTER: Szostak M
PROVIDER: S-EPMC3982934 | biostudies-literature | 2014 Feb
REPOSITORIES: biostudies-literature
Journal of the American Chemical Society 20140131 6
Highly chemoselective direct reduction of primary, secondary, and tertiary amides to alcohols using SmI2/amine/H2O is reported. The reaction proceeds with C-N bond cleavage in the carbinolamine intermediate, shows excellent functional group tolerance, and delivers the alcohol products in very high yields. The expected C-O cleavage products are not formed under the reaction conditions. The observed reactivity is opposite to the electrophilicity of polar carbonyl groups resulting from the n(X) → π ...[more]