Synfacts 2006(3): 0204-0204  
DOI: 10.1055/s-2006-931969
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Polysubstituted Pyrroles via Dihydro-1,2-oxazines

Contributor(s): Victor Snieckus, Robert Engqvist
G. Calvet, N. Blanchard, C. Kouklovsky*
Université d’Orsay, France
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
21. Februar 2006 (online)

Significance

A method for the synthesis of polysubstituted pyrroles via Diels-Alder adducts derived from the reaction of dienes with tert-butyl N-hydroxycarbamate is reported. The reaction of the dienes with tert-butyl N-oxocarbamate, derived by in situ oxidation from N-Boc-hydroxyl­amine leads to oxazines in good to excellent yields and regioselectivities from 55:45 to 2:98 depending on the diene. Reductive ring opening using NaBH4 in the presence of Mo(CO)6 gave the corresponding amino alcohols which, under MnO2 or Dess-Martin periodinane oxidative conditions and subsequent cyclization, led to the final pyrrole derivatives in excellent yields.