Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles

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Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles

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Title: Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles
Author: Formica, Michele; Sorin, Geoffroy; Farley, Alistair J. M.; Díaz Álvarez, Jesús; Paton, Robert S.; Dixon, Darren J.
Abstract: Se describe la primera adición enantioselectiva de sulfamidas-michael de alquil tioles a los alquilbencimidazoles, habilitada por un organocatalizador bifuncional de iminofosforano (BIMP). La fracción de iminofosforano del catalizador proporciona la basicidad necesaria para desprotonar al nucleófilo de tioles, mientras que el andamiaje quiral y el donante de H-bond controlan la selectividad facial. La reacción es de amplio alcance con respecto a los asociados de la reacción del tiol y el bencimidazol, con un rendimiento de hasta el 98% y un 96 : 4 er.The first enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles, enabled by a bifunctional iminophosphorane (BIMP) organocatalyst, is described. The iminophosphorane moiety of the catalyst provides the required basicity to deprotonate the thiol nucleophile while the chiral scaffold and H-bond donor control facial selectivity. The reaction is broad in scope with respect to the thiol and benzimidazole reaction partners with the reaction proceeding in up to 98% yield and 96 : 4 er.
URI: http://hdl.handle.net/10662/10901
Date: 2018


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