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Issue 24, 2017
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Enantioselective [2+2] annulation of simple aldehydes with isatin-derived ketimines via oxidative N-heterocyclic carbene catalysis

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Abstract

An asymmetric [2+2] annulation reaction through direct α-carbon functionalization of simple aldehydes via oxidative N-heterocyclic carbene catalysis is disclosed. These in situ generated triazolium enolate intermediates undergo a highly stereoselective Mannich reaction with isatin-derived ketimines followed by intramolecular lactamization to afford enantioenriched spirooxindole β-lactams bearing two vicinal stereogenic centers.

Graphical abstract: Enantioselective [2+2] annulation of simple aldehydes with isatin-derived ketimines via oxidative N-heterocyclic carbene catalysis

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Publication details

The article was received on 15 Feb 2017, accepted on 06 Mar 2017, published on 06 Mar 2017 and first published online on 06 Mar 2017


Article type: Communication
DOI: 10.1039/C7CC01232B
Citation: Chem. Commun., 2017,53, 3430-3433
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    Enantioselective [2+2] annulation of simple aldehydes with isatin-derived ketimines via oxidative N-heterocyclic carbene catalysis

    J. Xu, S. Yuan, J. Peng, M. Miao, Z. Chen and H. Ren, Chem. Commun., 2017, 53, 3430
    DOI: 10.1039/C7CC01232B

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