Bifunctional Iminophosphorane Catalysed Enantioselective Sulfa-Michael Addition of Alkyl Thiols to Alkenyl Benzimidazoles

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2018 Sep 14

PMID 30210771

Citations 10

Authors

Michele Formica

Geoffroy Sorin

Alistair J M Farley

Jesus Diaz

Robert S Paton

Darren J Dixon

Affiliations

Soon will be listed here.

Abstract

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.

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