Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes

Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydroamination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuterated amines, in ex...

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Bibliografiske detaljer
Main Authors: Zhu, Shaolin, Buchwald, Stephen Leffler
Andre forfattere: Massachusetts Institute of Technology. Department of Chemistry
Format: Article
Sprog:en_US
Udgivet: American Chemical Society (ACS) 2015
Online adgang:http://hdl.handle.net/1721.1/99676
https://orcid.org/0000-0003-3875-4775
Beskrivelse
Summary:Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydroamination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuterated amines, in excellent yields with high enantioselectivities. Furthermore, catalyst loading as low as 0.4 mol% could be employed to deliver product in undiminished yield and selectivity, demonstrating the practicality of this method for large-scale synthesis.