Asymmetric synthesis of Rauhut–Currier-type esters via Mukaiyama–Michael reaction to acylphosphonates under bifunctional catalysis
| Autor: | Jose Julian Aleman Lara, Jose Aleman, Sergio Diaz-Tendero Victoria, Víctor Laina, Roberto Del Río-Rodríguez, Jose Antonio Fernandez-Salas |
|---|---|
| Přispěvatelé: | UAM. Departamento de Química, UAM. Departamento de Química Orgánica |
| Rok vydání: | 2018 |
| Předmět: |
Enantioselectivity
Chemical parameters 010402 general chemistry 01 natural sciences Catalysis chemistry.chemical_compound Regioselectivity Chemical structure Materials Chemistry Organic chemistry Reactivity (chemistry) Bifunctional Chromatography 010405 organic chemistry Chemistry Metals and Alloys Enantioselective synthesis Asymmetric synthesis Química General Chemistry Mukaiyama Michael reaction humanities 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials Organocatalysis Ceramics and Composites Michael reaction Conjugate |
| Zdroj: | Biblos-e Archivo. Repositorio Institucional de la UAM instname Chemical Communications |
| ISSN: | 1364-548X 1359-7345 2015-6456 |
| DOI: | 10.1039/c8cc07561a |
| Popis: | 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 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) |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|