Organocatalytic Enantioselective Strecker Reaction with Seven-Membered Cyclic Imines

Abstract

[EN] A highly enantioselective Strecker reaction with dibenzo[b,f][1,4]oxazepines has been described using a dihydroquinine-derived thiourea as organocatalyst. The reaction affords chiral 10,11-dihydrodibenzo[b,f][1,4] oxazepine 11-carbonitrile derivatives in excellent yields (up to 99%) and excellent enantioselectivities (up to 98%) under mild reaction conditions. ; Financial support from the Agencia Estatal de Investigacion (Spanish Government) and Fondo Europeo de Desarrollo Regional (FEDER, European Union) (CTQ2017-84900-P) is acknowledged. C. V. thanks the Spanish Government for a Ramon y Cajal contract (RyC-2016-20187). Access to NMR, MS and X-ray facilities from the Servei central de suport a la investigacio experimental (SCSIE)-UV is also acknowledged. ; Lluna Galán, C.; Blay, G.; Fernández, I.; Muñoz Roca, MDC.; Pedro, JR.; Vila, C. (2018). Organocatalytic Enantioselective Strecker Reaction with Seven-Membered Cyclic Imines. Advanced Synthesis & Catalysis. 360(19):3662-3666. https://doi.org/10.1002/adsc.201800754 ; S ; 3662 ; 3666 ; 360 ; 19