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      • HARVEST
      • College of Arts and Science
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      Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes: Important Role for Water as an Additive

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      Date
      2020-12-15
      Author
      Rezazadeh Khalkhali, Mehran
      Wilde, Myron M. D.
      Gravel, Michel
      Publisher
      ACS Publications
      Type
      Article
      Peer Reviewed Status
      Peer Reviewed
      Metadata
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      Abstract
      The first highly enantioselective intermolecular Stetter reaction using simple enones is reported. A series of novel chiral BAC structures were designed and prepared. They were tested in the Stetter reaction with simple aldehydes and enones. The products were generated in excellent yields and enantioselectivities (up to 92% ee). Surprisingly, a substoichiometric amount of water was crucial to obtain high enantioselectivities. Chiral BACs were also shown to catalyze 1,6-conjugate addition reactions with paraquinone methides enantioselectively.
      Citation
      Rezazadeh Khalkhali, M.; Wilde, M. M. D.; Gravel, M. Org. Lett. 2021, 23. https://doi.org/10.1021/acs.orglett.0c03879
      URI
      http://hdl.handle.net/10388/13180
      DOI
      10.1021/acs.orglett.0c03879
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      • Chemistry
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