Intramolecular Schmidt reaction involving primary azidoalcohols under nonacidic conditions: synthesis of indolizidine (-)-167B.
A powerful intramolecular Schmidt reaction starting from primary azidoalcohols is reported. This approach involves a nonacidic activation of the alcohol via triflation. The synthetic potential offered by the mild reaction conditions is demonstrated by a highly selective synthesis of (-)-indolizidine 167B.
Kapat
Ajoy
A
University of Berne, Department of Chemistry and Biochemsitry, Freiestrasse 3, CH-3012 Berne, Switzerland.
Nyfeler
Erich
E
Giuffredi
Guy T
GT
Renaud
Philippe
P
D000438:Alcohols / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
C413205:167B indolizidine; D000438:Alcohols; D007212:Indolizines