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

Shaolin Zhu | Zendy; Stephen L. Buchwald | Zendy

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

Author(s) -

Shaolin Zhu,

Stephen L. Buchwald

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja509786v

Subject(s) - chemistry , hydroamination , markovnikov's rule , enantioselective synthesis , catalysis , hydroxylamine , yield (engineering) , selectivity , combinatorial chemistry , organic chemistry , regioselectivity , materials science , metallurgy

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.

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