Artículo
Asymmetric synthesis of dibenzo[b,d]azepines by Cu-catalyzed reductive or borylative cyclization
Autor/es | Rodríguez Salamanca, Patricia
Martín de la Calle, Rocío Rodríguez Bravo, Verónica Merino, Pedro Fernández Fernández, Rosario Fátima Lassaletta, José M. Hornillos, Valentín |
Departamento | Universidad de Sevilla. Departamento de Química orgánica |
Fecha de publicación | 2021 |
Fecha de depósito | 2022-03-22 |
Publicado en |
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Resumen | A copper-catalyzed asymmetric intramolecular reductive cyclization for the synthesis of dibenzo[b,d]azepines is described. Use of 2′-vinyl-biaryl-2-imines as substrates and in situ formed [CuI/(Ph-BPE)] as the catalyst ... A copper-catalyzed asymmetric intramolecular reductive cyclization for the synthesis of dibenzo[b,d]azepines is described. Use of 2′-vinyl-biaryl-2-imines as substrates and in situ formed [CuI/(Ph-BPE)] as the catalyst enables the synthesis of 7-membered bridged biarylamines containing both central and axial stereogenic elements in high yields (up to 98%) and with excellent diastereo- and enantioselectivities (>20 : 1 d.r., up to 99% ee). Moreover, the same catalyst was found to facilitate a related borylative cyclization to afford versatile boronic ester derivatives. Both reactions proceed under mild conditions (rt) and are applicable to a variety of substituted aromatic and heterocyclic derivatives. |
Agencias financiadoras | Ministerio de Ciencia e Innovación (MICIN). España Junta de Andalucía Gobierno de Aragón |
Identificador del proyecto | PID2019-106358GB-C21
PID2019-106358GB-C22 PID2019-104090RB-100 E34_20R P18-FR-3531 P18-FR-644 US1262867 US-1260906 |
Cita | Rodríguez Salamanca, P., Martín de la Calle, R., Rodríguez Bravo, V., Merino, P., Fernández Fernández, R.F., Lassaletta, J.M. y Hornillos, V. (2021). Asymmetric synthesis of dibenzo[b,d]azepines by Cu-catalyzed reductive or borylative cyclization. Chemical Science, 12 (46), 15291-15297. |
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10.1039_d1sc04980a.pdf | 1.750Mb | [PDF] | Ver/ | |