期刊
CHEMICAL SCIENCE
卷 9, 期 34, 页码 6969-6974出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc01804a
关键词
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资金
- EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine [EP/L015838/1]
- AstraZeneca
- Diamond Light Source
- Defence Science and Technology Laboratory
- Evotec
- GlaxoSmithKline
- Janssen
- Novartis
- Pfizer
- Syngenta
- Takeda
- UCB
- Vertex
- Universite Paris Descartes
- Spanish Ministry of Education, Culture and Sports
- National Science Foundation [ACI-1532235, ACI-1532236)]
- University of Colorado Boulder
- Colorado State University
- Extreme Science and Engineering Discovery Environment (XSEDE) [TG-CHE180006]
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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