Synlett 2007(19): 3022-3026  
DOI: 10.1055/s-2007-992361
LETTER
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Fluorination of Silylated 1,2-Oxazines to Access Fluorinated N,O-Heterocycles

Yu-hong Lama, Matthew N. Hopkinsona, Steven J. Stanwayb, Véronique Gouverneur*a
a Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA, UK
Fax: +44(1865)275644; e-Mail: veronique.gouverneur@chem.ox.ac.uk;
b Neurology and GI Centre of Excellence for Drug Discovery, GlaxoSmithKline, New Frontiers Science, Third Avenue, Harlow, Essex CM19 5AW, UK
Further Information

Publication History

Received 8 October 2007
Publication Date:
08 November 2007 (eFirst)

Abstract

The electrophilic fluorination of silylated N,O-heterocycles, prepared from a nitroso-Diels-Alder reaction of silylated dienes, afforded fluorinated 1,2-oxazines with the fluorine substituent on a stereogenic centre in moderate to high diastereoselectivities. The sense and level of diastereocontrol were found to be dependent of the substitution pattern of the heterocycle.