- Disulfonimide-Catalyzed Asymmetric Reduction of N-Alkyl Imines
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A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O has been developed. The reaction delivers Boc-protected N-alkyl amines with excellent yields and enantioselectivity. The method tolerates a large variety of alkyl amines, thus illustrating potential for a general reductive cross-coupling of ketones with diverse amines, and it was applied in the synthesis of the pharmaceuticals (S)-Rivastigmine, NPS R-568 Hydrochloride, and (R)-Fendiline. A chiral disulfonimide (DSI)-catalyzed asymmetric reduction of N-alkyl imines with Hantzsch esters as a hydrogen source in the presence of Boc2O was developed. The reaction delivers Boc-protected N-alkyl amines with excellent yields and enantioselectivity. The method was successfully applied to the synthesis of the pharmaceuticals (S)-Rivastigmine, NPS R-568 Hydrochloride, and (R)-Fendiline.
- Wakchaure, Vijay N.,Kaib, Philip S. J.,Leutzsch, Markus,List, Benjamin
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supporting information
p. 11852 - 11856
(2015/10/05)
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- Monoalkylation of primary amines and N-sulfinylamides
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An efficient monoalkylation of primary amines with primary or secondary alcohols catalyzed by Ra-Ni under mild conditions is described. The Royal Society of Chemistry.
- García Ruano, José Luis,Parra, Alejandro,Alemán, José,Yuste, Francisco,Mastranzo, Virginia M.
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supporting information; experimental part
p. 404 - 406
(2009/05/06)
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- ASYMMETRIC IMINE HYDROGENATION PROCESSES
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A process for the catalytic hydrogenation or asymmetric hydrogenation of imines of Formula (I) to the corresponding amines of Formula (II) is provided in which R1 is aryl ; R2 is aryl, cyclic, alkyl, alkenyl or alkynyl; and R3 is alky l. The catalytic system includes a ruthenium complex containing (1) a diamine and (2) a diphosphine or two monodentate phosphines ligands. Such process also relates to the asymmetric hydrogenation of prochiral imines to the chiral amines using chiral ruthenium complexes bearing chiral diphosphines or chiral monodentate phosphines and chiral diamines.
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Page/Page column 28
(2008/06/13)
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- Hydroamination of carbonyl compounds with oximes
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N-alkyl(cycloalkyl)benzylamines, p-fluorobenzylamines, (1-phenylethyl) amines, [1-(p-fluorophenyl)ethyl]amines were synthesized by hydroamination of aldehydes and ketones with oximes.
- Tarasevich,Kozlov
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p. 379 - 383
(2007/10/03)
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- Saponification agents. 2. Synthesis of arylisocyanates with ethyl lactate and their use in racemic bases saponification
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Reaction of the arylisocyanates 2a-c with ethyl (S)-(-)-lactate, followed by careful saponification, afforded the corresponding chiral acids (S)-(-)- 4a-c. The latter were successfully used for the resolution of various racemic bases belonging to both the ephedrine and α-aryl ethylamine series.
- Brown,Moudachirou
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p. 10309 - 10320
(2007/10/02)
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- SYNTHESIS OF ARYLIMINES FROM N-SILYLAMIDES AND ARYLLITHIUM COMPOUNDS
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Various arylimines were synthesized by the addition of N-silylated-N-alkyl- or N-aryl-amides to aryllithium compounds.
- Feringa, Ben L.,Jansen, F. G. A.
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p. 507 - 508
(2007/10/02)
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- Photochemical Reactions of Substituted Benzenes with Aliphatic Amines
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The products arising from the irradiation of diethylamine and t-butylamine with toluene, chlorobenzene, anisole, benzonitrile, benzyl fluoride, benzotrifluoride (α,α,α-trifluorotoluene), m-fluorobenzotrifluoride (α,α,α,m-tetrafluorotoluene), p-fluorotoluene, m-fluorotoluene, p-fluoroanisole, m-fluoroanisole, and 1,3-bis(trifluoromethyl)benzene, and of triethylamine with toluene, benzotrifluoride and 1,3-bis(trifluoromethyl)benzene, all at 254 nm, are described.Reaction pathways involving both substitution and 1,2- and 1,4-acyclic addition processes are observed and which predominates depends upon the arene substituent.The novel acyclic adduct, Me2C=CH-CH=CH-CH=NBut, is obtained from toluene and t-butylamine and, contrary to previous reports, chlorobenzene yields arene-amine 1:1 adducts as well as the amine α-substitution product (16); benzonitrile gives aniline derivatives with the primary and secondary amines.
- Gilbert, Andrew,Krestonosich, Stefan,Westover, David L.
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p. 295 - 302
(2007/10/02)
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