Taniaphos·AgF-catalyzed enantioselective 1,3-dipolar cycloaddition of stabilized azomethine ylides derived from 2,2-dimethoxyacetaldehyde
| Autor: | Alberto Cayuelas, Fernando P. Cossío, Olatz Larrañaga, Carmen Nájera, José M. Sansano, Abel de Cózar |
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| Přispěvatelé: | Universidad de Alicante. Departamento de Química Orgánica, Universidad de Alicante. Instituto Universitario de Síntesis Orgánica, Síntesis Asimétrica (SINTAS) |
| Rok vydání: | 2016 |
| Předmět: |
Enantioselective
010405 organic chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Azomethine ylide 2 2-Dimethoxyacetaldehyde 010402 general chemistry Dipolar cycloaddition 01 natural sciences Biochemistry Medicinal chemistry Silver(I) Cycloaddition 0104 chemical sciences Catalysis chemistry.chemical_compound Química Orgánica chemistry Taniaphos Drug Discovery 1 3-Dipolar cycloaddition Azomethine ylides BINAP |
| Zdroj: | RUA. Repositorio Institucional de la Universidad de Alicante Universidad de Alicante (UA) |
| ISSN: | 2010-2038 |
| Popis: | The enantioselective Taniaphos·silver fluoride-catalyzed enantioselective 1,3-dipolar cycloaddition using 2,2-dimethoxyacetaldehyde derived imino esters and maleimides is described. The employment of this complex allows the reaction in the absence of an extra base giving high yields and ee of the corresponding endo-cycloadducts. Calculations performed at B3LYP/6-31G*&LANL2DZ level of theory predicted the expected absolute stereochemistry for both BINAP and Taniaphos·silver fluoride-mediated cycloadditions, as well as the enantioselectivity and mild conditions of the reaction. Financial support was provided by the Spanish Ministerio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387, and Consolider Ingenio 2010, CSD2007-00006), the Spanish Ministerio de Economía y Competitividad (MINECO) (projects CTQ2013-43446-P, and CTQ2014-51912-REDC), FEDER, the Generalitat Valenciana (PROMETEO 2009/039 and PROMETEOII/2014/017), the University of Alicante, the Gobierno Vasco/Eusko Jaurlaritza (Grant IT673-13), and the Univeristy of the Basque Country UPV/EHU (UFI11/22 QOSYC). |
| Databáze: | OpenAIRE |
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