Synthesis of aminocyclobutanes through ring expansion of N-vinyl-beta-lactams

Lawrence L W Cheung; Andrei K Yudin

doi:10.1021/ol900118d

Synthesis of aminocyclobutanes through ring expansion of N-vinyl-beta-lactams

Org Lett. 2009 Mar 19;11(6):1281-4. doi: 10.1021/ol900118d.

Authors

Lawrence L W Cheung¹, Andrei K Yudin

Affiliation

¹ Department of Chemistry, University of Toronto, 80 St. George Street, Toronto M5S 3H6, Canada.

PMID: 19239262
DOI: 10.1021/ol900118d

Abstract

Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane-containing delta-lactams can be accessed from N-vinyl-beta-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lactam undergoes electrocyclization to furnish fused cyclobutane delta-lactams in a diastereoselective manner.

Publication types

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

MeSH terms

Catalysis
Combinatorial Chemistry Techniques
Cyclization
Cyclobutanes / chemical synthesis*
Cyclobutanes / chemistry
Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry*
Molecular Structure
beta-Lactams / chemical synthesis*
beta-Lactams / chemistry

Substances

Cyclobutanes
Heterocyclic Compounds
beta-Lactams