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Issue 28, 2011
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Enantioselective formal hydration of α,β-unsaturated acceptors: asymmetric conjugate addition of silicon and boron nucleophiles

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Abstract

The direct enantioselective 1,4-addition of water to α,β-unsaturated acceptors is an open challenge in asymmetric catalysis. Enantioselective conjugate addition of either silicon or boron nucleophiles and subsequent enantiospecific oxidative degradation of the carbon–element bond represents, however, an attractive detour. A single extra step thereby enables an indirect enantiocontrolled construction of (in a broader sense) aldols from α,β-unsaturated carbonyl and carboxyl compounds. While that strategy had been obvious for a long time, it was recent stunning progress in transition metal-catalysed activation of interelement linkages that brought about the solution to that long-standing problem. A concise introduction of existing protocols for stereoselective 1,4-addition of oxygen nucleophiles is followed by a comprehensive summary of the recent rapid advances in transition metal-catalysed (and metal-free) asymmetric conjugate transfer of nucleophilic silicon and boron onto α,β-unsaturated acceptors.

Graphical abstract: Enantioselective formal hydration of α,β-unsaturated acceptors: asymmetric conjugate addition of silicon and boron nucleophiles

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Publication details

The article was received on 26 Jan 2011, accepted on 04 Apr 2011 and first published on 28 Apr 2011


Article type: Feature Article
DOI: 10.1039/C1CC10528K
Citation: Chem. Commun., 2011,47, 7917-7932

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    Enantioselective formal hydration of α,β-unsaturated acceptors: asymmetric conjugate addition of silicon and boron nucleophiles

    E. Hartmann, D. J. Vyas and M. Oestreich, Chem. Commun., 2011, 47, 7917
    DOI: 10.1039/C1CC10528K

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