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Asymmetric synthesis of Rauhut–Currier-type esters via Mukaiyama–Michael reaction to acylphosphonates under bifunctional catalysis

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Abstract

A highly enantioselective organocatalytic Mukaiyama–Michael reaction of silyloxy dienes and α,β-unsaturated acyl phosphonates under bifunctional organocatalysis is presented. The new reactivity triggered by the catalyst conducted to Rauhut–Currier type esters, via a formal conjugate addition to α,β-unsaturated esters. This protocol proceeds under mild conditions with complete regioselectivity and excellent enantiocontrol.

Graphical abstract: Asymmetric synthesis of Rauhut–Currier-type esters via Mukaiyama–Michael reaction to acylphosphonates under bifunctional catalysis

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Publication details

The article was received on 18 Sep 2018, accepted on 22 Oct 2018 and first published on 23 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC07561A
Citation: Chem. Commun., 2018, Advance Article
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    Asymmetric synthesis of Rauhut–Currier-type esters via Mukaiyama–Michael reaction to acylphosphonates under bifunctional catalysis

    V. Laina-Martín, R. del Río-Rodríguez, S. Díaz-Tendero, J. A. Fernández-Salas and J. Alemán, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC07561A

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