Asymmetric synthesis of Rauhut-Currier-type esters via Mukaiyama-Michael reaction to acylphosphonates under bifunctional catalysis
Entidad
UAM. Departamento de Química; UAM. Departamento de Química OrgánicaEditor
Royal Society of ChemistryFecha de edición
2018-10-23Cita
10.1039/c8cc07561a
Chemical Communications 54.99 (2018): 13941-13944
ISSN
1359-7345 (print); 1364-548X (online)DOI
10.1039/c8cc07561aFinanciado por
We are grateful to the Spanish Government (CTQ2015-64561-R and CTQ2016-76061-P) and the European Research Council (ERCCG-UNBICAT, contract number: 647550). J. A. F.-S. and V. L.-M. thank the Spanish Government for a Juan de la Cierva Contract and the Universidad Auto´noma de Madrid for a predoctoral fellowship (FPI-UAM), respectively. Financial support from the Spanish Ministry of Economy and Competitiveness, through the ‘‘Maria de Maeztu’’ Program of Excellence in R&D (MDM-2014-0377), is also acknowledged. We acknowledge the generous allocation of computing time at the CCC (UAM)Proyecto
Gobierno de España. CTQ2015-64561-R; Gobierno de España. CTQ2016-76061-P; Gobierno de España. MDM-2014-0377; info:eu-repo/grantAgreement/EC/H2020/647550/EU//UNBICATVersión del editor
https://doi.org/10.1039/c8cc07561aMaterias
Asymmetric synthesis; Catalysis; Chemical structure; Chemical parameters; Chromatography; Enantioselectivity; Regioselectivity; Mukaiyama Michael reaction; QuímicaDerechos
© 2018 The Royal Society of ChemistryResumen
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
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Google Scholar:Laina-Martín, Víctor
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Del Río-Rodríguez, Roberto
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Díaz-Tendero Victoria, Sergio
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Fernández-Salas, Jose A.
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Alemán Lara, José Julián
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