Organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates of isatins

Beilstein J Org Chem. 2012:8:1241-5. doi: 10.3762/bjoc.8.139. Epub 2012 Aug 6.

Abstract

The investigation of a Lewis base catalyzed asymmetric allylic amination of Morita-Baylis-Hillman carbonates derived from isatins afforded an electrophilic pathway to access multifunctional oxindoles bearing a C3-quaternary stereocenter, provided with good to excellent enantioselectivity (up to 94% ee) and in high yields (up to 97%).

Keywords: 2-oxindoles; Morita–Baylis–Hillman carbonates; allylic amination; asymmetric organocatalysis; quaternary chiral center.