Diastereoselective Control of Intramolecular Aza-Michael Reactions Using Achiral Catalysts

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 rang...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2011-10, Vol.13 (20), p.5556-5559
Main Authors: Zhong, Cheng, Wang, Yikai, Hung, Alvin W, Schreiber, Stuart L, Young, Damian W
Format: Article
Language:English
Subjects:
Aza Compounds - chemistry
Carbamates - chemistry
Catalysis
Combinatorial Chemistry Techniques
Ketones - chemical synthesis
Ketones - chemistry
Molecular Structure
Palladium - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202276h