Stereo- and regioselectivity of the hetero-Diels-Alder reaction of nitroso derivatives with conjugated dienes.
The hetero-Diels-Alder reaction between a nitroso dienophile and a conjugated diene to give the 3,6-dihydro-2H-1,2-oxazine scaffold is useful for the synthesis of many biologically interesting molecules due to the diverse opportunities created by subsequent transformations of the resulting 1,2-oxazine ring. This review discusses the rationale for the observed regio- and stereoselectivity and the methods developed in recent years used to control and improve the stereo- and regioselectivity for the synthesis of 1,2-oxazine scaffolds.
Department of Organic Chemistry, Faculty of Science, Palacký University, 17. Listopadu 12, 77146 Olomouc, Czech Republic.
Lucie
L
Brulíková
Department of Medicinal Chemistry, Institute of Molecular and Translational Medicine, Hněvotínská 5, 77900 Olomouc, Czech Republic.
Aidan
A
Harrison
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA.
Marvin J
MJ
Miller
Department of Medicinal Chemistry, Institute of Molecular and Translational Medicine, Hněvotínská 5, 77900 Olomouc, Czech Republic.
Jan
J
Hlaváč
diene; hetero-Diels–Alder; nitroso compounds; regioselectivity; stereoselectivity