Pd-catalyzed carboamination of oxazolidin-2-ones: a stereoselective route to trans-2,5-disubstituted pyrrolidines.

Org Lett

Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, Michigan 48109-1055, USA.

Published: May 2010

Palladium-catalyzed carboamination reactions between aryl bromides and 4-(but-3-enyl)-substituted oxazolidin-2-ones are described. These transformations afford bicyclic oxazolidin-2-one derivatives that can be converted to trans-2,5-disubstituted pyrrolidines in one step. The starting materials are easily prepared from amino acid precursors, and products that contain up to three stereocenters are generated with >20:1 dr.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2873168PMC
http://dx.doi.org/10.1021/ol1006828DOI Listing

Publication Analysis

Top Keywords

trans-25-disubstituted pyrrolidines
8
pd-catalyzed carboamination
4
carboamination oxazolidin-2-ones
4
oxazolidin-2-ones stereoselective
4
stereoselective route
4
route trans-25-disubstituted
4
pyrrolidines palladium-catalyzed
4
palladium-catalyzed carboamination
4
carboamination reactions
4
reactions aryl
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!