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Organic letters DOI:10.1021/ol202276h

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

Publication TypeJournal Article
Year of Publication2011
AuthorsZhong, C, Wang, Y, Hung, AW, Schreiber, SL, Young, DW
JournalOrganic letters
Volume13
Issue20
Pages5556-9
Date Published2011/10/21
ISSN1523-7060
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.

URLhttp://dx.doi.org/10.1021/ol202276h
DOI10.1021/ol202276h
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/21916463?dopt=Abstract