Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 8, Pages 2212-2215Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201610105
Keywords
asymmetric synthesis; chirality transfer; rearrangement; sulfoxides; ynamides
Categories
Funding
- ERCStG FLATOUT
- University of Vienna
- Austrian Academy of Sciences
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A general, asymmetric redox arylation of ynamides and thioalkynes with chiral sulfoxides is reported. This is the first example of a general 1,4-chirality transfer from sulfur to a carbon stereocenter through a sulfonium [3,3]-sigmatropic rearrangement. This reaction delivers alpha-arylated thioesters and amides under mild conditions in an atom-economical manner. The products are formed in high yields with enantiomeric ratios up to 99.5:0.5. Quantum chemical calculations suggest a mechanism for the chirality transfer from sulfur to carbon and explain the experimentally observed correlation of the enantioselectivity with both the catalyst and the substrate.
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