Enantioselective reduction of N-alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions | Zendy

Dan M. Mercea | Zendy; Michael G. Howlett | Zendy; Adam D. Piascik | Zendy; Daniel J. Scott | Zendy; Alan Steven | Zendy; Andrew E. Ashley | Zendy; Matthew J. Fuchter | Zendy

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Enantioselective reduction of N-alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions

Author(s) -

Dan M. Mercea,

Michael G. Howlett,

Adam D. Piascik,

Daniel J. Scott,

Alan Steven,

Andrew E. Ashley,

Matthew J. Fuchter

Publication year - 2019

Publication title -

chemical communications

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.837

H-Index - 333

eISSN - 1364-548X

pISSN - 1359-7345

DOI - 10.1039/c9cc02900a

Subject(s) - enantioselective synthesis , catalysis , alkyl , frustrated lewis pair , chemistry , reduction (mathematics) , ion , lewis acids and bases , combinatorial chemistry , medicinal chemistry , organic chemistry , mathematics , geometry

Enantioselective reduction of ketimines was demonstrated using chiral N-heterocyclic carbene (NHC)-stabilised borenium ions in frustrated Lewis pair catalysis. High levels of enantioselectivity were achieved for substrates featuring secondary N-alkyl substituents. Comparative reactivity and mechanistic studies identify key determinants required to achieve useful enantioselectivity and represent a step forward in the further development of enantioselective FLP methodologies.

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