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

Dan Mercea; Michael Howlett; Adam Piascik; Daniel Scott; Alan Steven; Andrew Ashley; Matthew J. Fuchter

doi:10.1039/C9CC02900A

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

Dan Mercea, Michael Howlett, Adam Piascik, Daniel Scott, Alan Steven, Andrew Ashley, Matthew J. Fuchter

Department of Chemistry

Imperial College London

Research output: Contribution to journal › Article › peer-review

31 Citations (SciVal)

Abstract

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.

Original language	English
Pages (from-to)	7077-7080
Journal	Chemical Communications
Volume	55
DOIs	https://doi.org/10.1039/C9CC02900A
Publication status	Published - 22 May 2019

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

abstract = "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.",

author = "Dan Mercea and Michael Howlett and Adam Piascik and Daniel Scott and Alan Steven and Andrew Ashley and Fuchter, {Matthew J.}",

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T1 - Enantioselective reduction of N-alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions

AU - Mercea, Dan

AU - Howlett, Michael

AU - Piascik, Adam

AU - Scott, Daniel

AU - Steven, Alan

AU - Ashley, Andrew

AU - Fuchter, Matthew J.

PY - 2019/5/22

Y1 - 2019/5/22

N2 - 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.

AB - 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.

U2 - 10.1039/C9CC02900A

DO - 10.1039/C9CC02900A

M3 - Article

SN - 1359-7345

VL - 55

SP - 7077

EP - 7080

JO - Chemical Communications

JF - Chemical Communications

ER -

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

Abstract

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