STEREOSELECTIVE SYNTHESIS OF BICYCLIC PYRROLIDINES AND PIPERIDINES VIA THE REDUCTIVE ALKYLATION OF AZIDES WITH ORGANYLDICHLOROBORANES - INTRAMOLECULAR NUCLEOPHILIC-SUBSTITUTION TANDEM SEQUENCE

Authors
JEGO JM CARBONI B YOUSSOFI A VAULTIER M
Citation
Jm. Jego et al., STEREOSELECTIVE SYNTHESIS OF BICYCLIC PYRROLIDINES AND PIPERIDINES VIA THE REDUCTIVE ALKYLATION OF AZIDES WITH ORGANYLDICHLOROBORANES - INTRAMOLECULAR NUCLEOPHILIC-SUBSTITUTION TANDEM SEQUENCE, Synlett, (8), 1993, pp. 595-597
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
8
Year of publication
1993
Pages
595 - 597
Database
ISI
SICI code
0936-5214(1993):8<595:SSOBPA>2.0.ZU;2-B
Abstract
Omega-halogenoalkyldichloroboranes are easily prepared in a stereocont rolled manner by hydroboration of omega-bromoalkylcycloalkenes or Diel s-Alder reaction of (E)-alkenyldichloroboranes. Amination with benzyla zide followed by an intramolecular nucleophilic substitution afforded the corresponding trans-pyrrolidines or piperidines.