A NEW METHOD TO GENERATE ALPHA-AMINOALKYL RADICALS - TREATMENT OF METHYL ALPHA-AMINO SELENOESTERS WITH HYDRIDE REAGENTS - SYNTHESIS OF 6-AZABICYCLO[3.2.1]OCTANES BY RADICAL CYCLIZATION

Authors
QUIRANTE J ESCOLANO C BONJOCH J
Citation
J. Quirante et al., A NEW METHOD TO GENERATE ALPHA-AMINOALKYL RADICALS - TREATMENT OF METHYL ALPHA-AMINO SELENOESTERS WITH HYDRIDE REAGENTS - SYNTHESIS OF 6-AZABICYCLO[3.2.1]OCTANES BY RADICAL CYCLIZATION, Synlett, (2), 1997, pp. 179
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
2
Year of publication
1997
Database
ISI
SICI code
0936-5214(1997):2<179:ANMTGA>2.0.ZU;2-1
Abstract
A new method to generate alpha-aminoalkyl radicals and its application to the synthesis of 6-azabicyclo[3.2.1]octanes is described. alpha-Am ino selenoesters on heating with Bu(3)SnH or (Me(3)Si)(3)SiH undergo d ecarbonylation of the initially formed acyl radical to give the corres ponding alpha-amino radical which could be trapped intramolecularly wi th a double bond bearing an electron-withdrawing group.