Stereo- and regioselectivity of the hetero-Diels-Alder reaction of nitroso derivatives with conjugated dienes

Beilstein J Org Chem. 2016 Sep 1:12:1949-1980. doi: 10.3762/bjoc.12.184. eCollection 2016.


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.

Keywords: diene; hetero-Diels–Alder; nitroso compounds; regioselectivity; stereoselectivity.

Publication types

  • Review