Pd(II)-catalyzed intramolecular 1,2-aminoalkylation of conjugated 1,3-dienes for the synthesis of pyrrolizidines

Dong Xing; Dan Yang

doi:10.1021/ol401901h

Pd(II)-catalyzed intramolecular 1,2-aminoalkylation of conjugated 1,3-dienes for the synthesis of pyrrolizidines

Org Lett. 2013 Sep 6;15(17):4370-3. doi: 10.1021/ol401901h. Epub 2013 Aug 27.

Authors

Dong Xing¹, Dan Yang

Affiliation

¹ Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China.

PMID: 23980544
DOI: 10.1021/ol401901h

Abstract

A palladium(II)-catalyzed tandem cyclization reaction involving an intramolecular 1,2-aminoalkylation of N-4,6-dienyl β-keto amides has been developed. This process provides an efficient method for the rapid assembly of pyrrolizidines starting from linear substrates in moderate to good yields and high to excellent diastereoselectivities.

Publication types

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

MeSH terms

Alkadienes / chemistry*
Alkylation
Amides / chemistry*
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Molecular Structure
Palladium / chemistry*
Pyrrolizidine Alkaloids / chemical synthesis*
Pyrrolizidine Alkaloids / chemistry
Stereoisomerism

Substances

Alkadienes
Amides
Pyrrolizidine Alkaloids
Palladium