Direct chemoselective allylation of inert amide carbonyls

Yukiko Oda; Takaaki Sato; Noritaka Chida

doi:10.1021/ol3000316

Direct chemoselective allylation of inert amide carbonyls

Org Lett. 2012 Feb 3;14(3):950-3. doi: 10.1021/ol3000316. Epub 2012 Jan 19.

Authors

Yukiko Oda¹, Takaaki Sato, Noritaka Chida

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Yokohama 223-8522, Japan.

PMID: 22260368
DOI: 10.1021/ol3000316

Abstract

Direct allylation of inert amide carbonyls utilizing the Schwartz reagent afforded either substituted tertiary or secondary amines. A preactivation step was successfully avoided, which is generally a requisite to increase the electrophilicity of amides. The reaction exhibited remarkable functional group tolerance and proceeded even in the presence of methyl esters and nitro groups.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Allyl Compounds / chemistry*
Amides / chemistry*
Molecular Structure

Substances

Allyl Compounds
Amides