Issue 20, 2023

Phosphine-catalyzed asymmetric aza-Morita–Baylis–Hillman reaction of endocyclic ketimines and activated alkenes

Abstract

A novel phosphine-catalyzed asymmetric aza-Morita–Baylis–Hillman reaction of endocyclic ketimines with vinyl ketone or acrolein has been presented. This approach resulted in densely functionalized adducts with moderate to high yields and enantioselectivities (up to 97% yield, up to 97% ee), with the feature of a C2 tetra-substituted chiral center on a 3-oxindole scaffold. A wide variety of substrates were compatible with this methodology, and diverse enantiomeric products could be obtained through a catalyst switching strategy. A series of transformations further demonstrated the utility of this methodology.

Graphical abstract: Phosphine-catalyzed asymmetric aza-Morita–Baylis–Hillman reaction of endocyclic ketimines and activated alkenes

Supplementary files

Article information

Article type
Research Article
Submitted
08 Goue. 2023
Accepted
01 Gwen. 2023
First published
11 Gwen. 2023

Org. Chem. Front., 2023,10, 5076-5082

Phosphine-catalyzed asymmetric aza-Morita–Baylis–Hillman reaction of endocyclic ketimines and activated alkenes

Y. Lu, F. Zhu, X. Liu and D. Wang, Org. Chem. Front., 2023, 10, 5076 DOI: 10.1039/D3QO01047C

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