Brønsted acid versus phase-transfer catalysis in the enantioselective transannular aminohalogenation of enesultams
| Autor: | Javier Luis‐Barrera, Sandra Rodriguez, Uxue Uria, Efraim Reyes, Liher Prieto, Luisa Carrillo, Manuel Pedrón, Tomás Tejero, Pedro Merino, Jose L. Vicario |
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| Přispěvatelé: | Ministerio de Ciencia, Innovación y Universidades (España), Agencia Estatal de Investigación (España), European Commission, Gobierno de Aragón, Eusko Jaurlaritza, Ministerio de Educación (España), Universidad de Zaragoza |
| Jazyk: | angličtina |
| Rok vydání: | 2022 |
| Předmět: | |
| ISSN: | 2020-1184 |
| Popis: | We have studied the enantioselective transannular aminohalogenation reaction of unsaturated medium-sized cyclic benzosulfonamides by using both chiral Brønsted acid and phase-transfer catalysis. Under optimized conditions, a variety of bicyclic adducts can be obtained with good yields and high enantioselectivities. The mechanism of the reaction was also studied by using computational tools; we observed that the reaction involves the participation of a conformer of the nine-membered cyclic substrate with planar chirality in which the stereochemical outcome is controlled by the relative reactivity of the two pseudorotational enantiomers when interacting with the chiral catalyst. The authors thank the Spanish Ministerio de Ciencia, Innovación y Universidades (FEDER PID2020-118422GB−I00 and FEDER PID2019-104090RB-100), the Basque Government (Grupos IT1558-22 and postdoctoral contract to J.L.-B.) and the Regional Government of Aragon (Grupos 17R-34) for financial support. Predoctoral FPU fellowship to S.R. from the Spanish Ministry of Education and to M.P. from Government of Aragon are also acknowledged. The authors thankfully acknowledge the resources from the super-computers “Memento” and “Cierzo”, technical expertise and assistance provided by BIFI-ZCAM (Universidad de Zaragoza, Spain). |
| Databáze: | OpenAIRE |
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