Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 12, Pages 3903-3907Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201814242
Keywords
asymmetric synthesis; copper; homogeneous catalysis; propargylic substitution; tertiary sulfones
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Funding
- CERCA Program/Generalitat de Catalunya
- ICREA
- Spanish MINECO [CTQ2017-88920-P]
- AGAUR [2017-SGR-232]
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Tertiary propargylic sulfones are of significant importance in organic synthesis and medicinal chemistry, but to date no general asymmetric synthesis approach has been developed. We disclose a versatile copper-catalyzed sulfonylation of propargylic cyclic carbonates using sodium sulfinates that allows the construction of propargylic sulfones featuring elusive quaternary stereocenters. This method provides the first successful example of such an enantioselective propargylic sulfonylation, features high asymmetric induction, wide functional group tolerance, and scalability, and enables attractive product diversification.
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