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Issue 45, 2008
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Asymmetric catalytic aza-Morita–Baylis–Hillman reaction (aza-MBH): an interesting functional group-caused reversal of asymmetric induction

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Abstract

A highly efficient aza-Morita–Baylis–Hillman reaction (aza-MBH reaction) of N-tosyl salicylaldehyde imines with α,β-unsaturated ketones has been achieved by using β-isocupreidine (β-ICPD) as the catalyst (10 mol%) to give the corresponding adducts in good to high yields (90%–quant.) and excellent ee’s (up to 99% ee), with adducts showing the opposite absolute configuration to that of those obtained in the similar aza-MBH reaction of N-tosyl aldimines with α,β-unsaturated ketones.

Graphical abstract: Asymmetric catalytic aza-Morita–Baylis–Hillman reaction (aza-MBH): an interesting functional group-caused reversal of asymmetric induction

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Publication details

The article was received on 20 Aug 2008, accepted on 19 Sep 2008 and first published on 15 Oct 2008


Article type: Communication
DOI: 10.1039/B814500H
Citation: Chem. Commun., 2008,0, 6025-6027

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    Asymmetric catalytic aza-Morita–Baylis–Hillman reaction (aza-MBH): an interesting functional group-caused reversal of asymmetric induction

    M. Shi, M. Qi and X. Liu, Chem. Commun., 2008, 0, 6025
    DOI: 10.1039/B814500H

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