Diastereoselective control of intramolecular aza-Michael reactions using achiral catalysts.

Org Lett
Authors
Keywords
Abstract

An intramolecular aza-Michael reaction with a Cbz carbamate and an enone is reported to result in 3,5-disubstituted nitrogen-containing heterocycles. Either cis or trans isomers were obtained selectively using chiral substrates and an achiral Pd(II) complex or strong Brønsted acid catalysis. A range of substrates undergoes these selective transformations. Functionalization of the resulting products yielding bicyclic heterocycles is also demonstrated.

Year of Publication
2011
Journal
Org Lett
Volume
13
Issue
20
Pages
5556-9
Date Published
2011 Oct 21
ISSN
1523-7052
DOI
10.1021/ol202276h
PubMed ID
21916463
Links
Grant list
P50 GM069721 / GM / NIGMS NIH HHS / United States