Bifunctional Iminophosphorane Catalyzed Amide Enolization for Enantioselective Cyclohexadienone Desymmetrization

• Published in: Angewandte Chemie International Edition Vol. 63; no. 5; pp. e202315401 - n/a
• Main Authors: Poh, Charmaine Y. X., Rozsar, Daniel, Yang, Jinchao, Christensen, Kirsten E., Dixon, Darren J.
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 25.01.2024; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: asymmetric catalysis; Chemistry; Chemistry, Multidisciplinary; conjugate Addition; C−C bond formation; Enantiomers; enantioselectivity; organocatalysis; Physical Sciences; Science & Technology; conjugate Addition; enantioselectivity; organocatalysis; ALKYL THIOLS; C-C bond formation; ACIDITIES; SULFA-MICHAEL ADDITION; ESTERS; CRYSTAL-STRUCTURES; ALPHA; asymmetric catalysis; ASYMMETRIC TRANSFORMATIONS; C−C bond formation

The organocatalytic enolization of 2‐arylacetamides, followed by an enantioselective intramolecular conjugate addition to tethered 2,5‐cyclohexadienones, yielding 3D fused N‐heterocycles, is described. The transformation represents the first strong activating group‐free activation of carboxamides vi...