Issue 1, 2016

N-Heterocyclic carbene-catalyzed [4 + 2] annulation of α,β-unsaturated carboxylic acids: enantioselective synthesis of dihydropyridinones and spirocyclic oxindolodihydropyridinones

Abstract

The N-heterocyclic carbene-catalyzed generation of dienoate from α,β-unsaturated carboxylic acid via the in situ formed mixed anhydride, and the following [4 + 2] annulation with hydrazones and isatin-derived imines was developed, affording the corresponding dihydropyridinones and spirocyclic oxindolodihydropyridinones, respectively, in moderate to good yields with good to excellent enantioselectivities.

Graphical abstract: N-Heterocyclic carbene-catalyzed [4 + 2] annulation of α,β-unsaturated carboxylic acids: enantioselective synthesis of dihydropyridinones and spirocyclic oxindolodihydropyridinones

Supplementary files

Article information

Article type
Research Article
Submitted
30 Way 2015
Accepted
14 Xim 2015
First published
16 Xim 2015

Org. Chem. Front., 2016,3, 77-81

N-Heterocyclic carbene-catalyzed [4 + 2] annulation of α,β-unsaturated carboxylic acids: enantioselective synthesis of dihydropyridinones and spirocyclic oxindolodihydropyridinones

W. Jia, H. Zhang, C. Zhang, Z. Gao and S. Ye, Org. Chem. Front., 2016, 3, 77 DOI: 10.1039/C5QO00301F

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