Decarbonylative radical cyclization of alpha-amino selenoesters upon electrophilic alkenes. A general method for the 6-azabicyclo[3.2.1]octane synthesis

Josefina Quirante; Xavier Vila; Carmen Escolano; Josep Bonjoch

doi:10.1021/jo0163849

Decarbonylative radical cyclization of alpha-amino selenoesters upon electrophilic alkenes. A general method for the 6-azabicyclo[3.2.1]octane synthesis

J Org Chem. 2002 Apr 5;67(7):2323-8. doi: 10.1021/jo0163849.

Authors

Josefina Quirante¹, Xavier Vila, Carmen Escolano, Josep Bonjoch

Affiliation

¹ Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain.

PMID: 11925248
DOI: 10.1021/jo0163849

Abstract

alpha-Amino selenoester-tethered electronically poor alkenes on treatment with tributyltin hydride or TTMSS undergo intramolecular radical cyclization to provide 6-azabicyclo[3.2.1]octanes through 1-aminomethyl radical intermediates.