Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst

Ernest Salomó; Albert Gallen; Giuseppe Sciortino; Gregori Ujaque; Arnald Grabulosa; Agustí Lledós; Antoni Riera; Xavier Verdaguer

doi:10.1021/jacs.8b11547

Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst

Ernest Salomó, Albert Gallen, Giuseppe Sciortino, Gregori Ujaque, Arnald Grabulosa, Agustí Lledós, Antoni Riera, Xavier Verdaguer

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34 Citations (Scopus)

Abstract

Copyright © 2018 American Chemical Society. A novel cationic [IrH(THF)(P,N)(imine)] [BAr F ] catalyst containing a P-stereogenic MaxPHOX ligand is described for the direct asymmetric hydrogenation of N-methyl and N-alkyl imines. This is the first catalytic system to attain high enantioselectivity (up to 94% ee) in this type of transformation. The labile tetrahydrofuran ligand allows for effective activation and reactivity, even at low temperatures. Density functional theory calculations allowed the rationalization of the stereochemical course of the reaction.

Original language	English
Pages (from-to)	16967-16970
Journal	Journal of the American Chemical Society
Volume	140
DOIs	https://doi.org/10.1021/jacs.8b11547
Publication status	Published - 12 Dec 2018

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title = "Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst",

abstract = "Copyright {\textcopyright} 2018 American Chemical Society. A novel cationic [IrH(THF)(P,N)(imine)] [BAr F ] catalyst containing a P-stereogenic MaxPHOX ligand is described for the direct asymmetric hydrogenation of N-methyl and N-alkyl imines. This is the first catalytic system to attain high enantioselectivity (up to 94% ee) in this type of transformation. The labile tetrahydrofuran ligand allows for effective activation and reactivity, even at low temperatures. Density functional theory calculations allowed the rationalization of the stereochemical course of the reaction.",

author = "Ernest Salom{\'o} and Albert Gallen and Giuseppe Sciortino and Gregori Ujaque and Arnald Grabulosa and Agust{\'i} Lled{\'o}s and Antoni Riera and Xavier Verdaguer",

year = "2018",

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doi = "10.1021/jacs.8b11547",

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T1 - Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst

AU - Salomó, Ernest

AU - Gallen, Albert

AU - Sciortino, Giuseppe

AU - Ujaque, Gregori

AU - Grabulosa, Arnald

AU - Lledós, Agustí

AU - Riera, Antoni

AU - Verdaguer, Xavier

PY - 2018/12/12

Y1 - 2018/12/12

N2 - Copyright © 2018 American Chemical Society. A novel cationic [IrH(THF)(P,N)(imine)] [BAr F ] catalyst containing a P-stereogenic MaxPHOX ligand is described for the direct asymmetric hydrogenation of N-methyl and N-alkyl imines. This is the first catalytic system to attain high enantioselectivity (up to 94% ee) in this type of transformation. The labile tetrahydrofuran ligand allows for effective activation and reactivity, even at low temperatures. Density functional theory calculations allowed the rationalization of the stereochemical course of the reaction.

AB - Copyright © 2018 American Chemical Society. A novel cationic [IrH(THF)(P,N)(imine)] [BAr F ] catalyst containing a P-stereogenic MaxPHOX ligand is described for the direct asymmetric hydrogenation of N-methyl and N-alkyl imines. This is the first catalytic system to attain high enantioselectivity (up to 94% ee) in this type of transformation. The labile tetrahydrofuran ligand allows for effective activation and reactivity, even at low temperatures. Density functional theory calculations allowed the rationalization of the stereochemical course of the reaction.

U2 - 10.1021/jacs.8b11547

DO - 10.1021/jacs.8b11547

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SN - 0002-7863

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SP - 16967

EP - 16970

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

ER -

Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst

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