Regioselective and Enantioselective Copper‐Catalyzed Hydroaminocarbonylation of Unactivated Alkenes and Alkynes

Abstract: Given the prevalence of amide backbones in marketed pharmaceuticals and their ubiquity as critical binding units in natural peptides and proteins, it remains important to develop novel methods to construct amide bonds. We report here a general method for the anti‐Markovnikov hydroaminocarbonylation of unactivated alkenes under mild conditions, using copper catalysis in combination with hydroxylamine electrophile reagents and poly (methylhydrosiloxane) (PMHS) as a cheap and environmentally friendly hydride source. The reaction tolerates a variety of functional groups and efficiently converts unactivated terminal alkenes, 1,1‐disubstituted alkenes, and cyclic alkenes to the corresponding amides with exclusive anti‐Markovnikov selectivity (and high enantioselectivities/diastereoselectivities). Additionally, with minimal modification of the reaction conditions, alkynes can also undergo tandem hydrogenation‐hydroaminocarbonylation to alkyl amides.

Objekt anzeigen

• Standort: Deutsche Nationalbibliothek Frankfurt am Main
• Umfang: Online-Ressource
• Sprache: Englisch

Verweise und Beziehungen

• Erschienen in: Regioselective and Enantioselective Copper‐Catalyzed Hydroaminocarbonylation of Unactivated Alkenes and Alkynes ; day:28 ; month:08 ; year:2023 ; extent:8 ; Angewandte Chemie / International edition. International edition ; (28.08.2023) (gesamt 8)

Beteiligte, Orts- und Zeitangaben

• Urheber: Yuan, Yang ; Zhang, Youcan ; Li, Wenbo ; Zhao, Yanying ; Wu, Xiao-Feng

Weitere Informationen

• DOI: 10.1002/anie.202309993
• URN: urn:nbn:de:101:1-2023082915010771391810
• Rechteinformation: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.