Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 12, Pages 4959-4964Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915470
Keywords
alkynes; axially chiral compounds; sulfide catalysis; synthetic methods; thiolation
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Funding
- National Natural Science Foundation of China [21772239, 91856109, 21901261]
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The enantioselective construction of axially chiral compounds by electrophilic carbothiolation of alkynes is disclosed for the first time. This enantioselective transformation is enabled by the use of a Ts-protected bifunctional sulfide catalyst and Ms-protected ortho-alkynylaryl amines (Ts=tosyl; Ms=mesyl). Both electrophilic arylthiolating and electrophilic trifluoromethylthiolating reagents are suitable for this reaction. The obtained products of axially chiral vinyl-aryl amino sulfides can be easily converted into biaryl amino sulfides, biaryl amino sulfoxides, biaryl amines, vinyl-aryl amines, and other valuable difunctionalized compounds.
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