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Issue 24, 2016
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Direct conjugate alkylation of α,β-unsaturated carbonyls by TiIII-catalysed reductive umpolung of simple activated alkenes

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Abstract

The titanium(III)-catalysed cross-selective reductive umpolung of Michael-acceptors represents a unique direct conjugate β-alkylation reaction. It allows the cross-selective preparation of 1,6- and 1,4-difunctionalised building blocks without the requirement of stoichiometric organometallic reagents. In this full paper, the development and scope of the titanium(III)-catalysed cross-selective reductive umpolung of Michael-acceptors is described. Based on the observed selectivities and additional mechanistic experiments a refined mechanistic proposal is presented.

Graphical abstract: Direct conjugate alkylation of α,β-unsaturated carbonyls by TiIII-catalysed reductive umpolung of simple activated alkenes

  • This article is part of the themed collection: New Talent
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Publication details

The article was received on 22 Dec 2015, accepted on 15 Jan 2016 and first published on 25 Jan 2016


Article type: Paper
DOI: 10.1039/C5OB02631H
Org. Biomol. Chem., 2016,14, 5673-5682
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    Direct conjugate alkylation of α,β-unsaturated carbonyls by TiIII-catalysed reductive umpolung of simple activated alkenes

    P. Bichovski, T. M. Haas, M. Keller and J. Streuff, Org. Biomol. Chem., 2016, 14, 5673
    DOI: 10.1039/C5OB02631H

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