(R,R)-and (S,S)-N,N'-dimethyl-1,2-diphenylethylene-1,2-diamine

(R,R)- and (S,S)-N,N′-dimethyl-1,2-diphenylethylene-1,2-diamine intermediate: N-Methylbenzimine intermediate: meso- and dl-N,N′-Dimethyl-1,2-diphenylethylenediamine intermediate: dl-N,N′-Dimethyl-1,2-diphenylethylene-diamine product: (R,R)-(+)-N,N′-Dimethyl-1,2-diphenylethylenediamine product: (S,S)-(−)-N,N′-Dimethyl-1,2-diphenylethylenediamine byproduct: 2-5% of N-methylbenzylamine Keywords: addition, to CO; coupling; deprotection, nitrogen; enamine or imine formation; rearrangements; resolution

[1]  A. Alexakis,et al.  Isomerization of meso Diamines into their C2 Symmetrical d,l Isomers , 1998 .

[2]  A. Alexakis,et al.  Practical and efficient synthesis of C2 symmetrical diamines with Zn/Me3SiCl , 1998 .

[3]  A. Alexakis,et al.  Preparation of chiral hexahydroquinolizinones and tetrahydroindolizinones by regio- and diastereoselective sonochemical cyclization of chiral dihydropyridines , 1996 .

[4]  A. Alexakis,et al.  Monoaminals of glyoxal: versatile chirons. , 1995 .

[5]  J. S. Sandhu,et al.  Novel reductive coupling of aldimines to vicinal diamines , 1995 .

[6]  A. Alexakis,et al.  Enantioselective ortho-lithiation of benzaldehyde chromiumtricarbonyl complex , 1995 .

[7]  A. Alexakis,et al.  Chiral Aminal Templates - Diastereoselective Addition To Hydrazones - An Asymmetric-synthesis of Alpha-amino Aldehydes , 1995 .

[8]  M. Shimizu,et al.  Highly Enantioselective Imino Pinacol Coupling Leading to the Synthesis of 1,2-Diphenylethylenediamine Derivatives , 1995 .

[9]  A. Alexakis,et al.  Enantioselective ortho-Lithiation of Aminals of benzaldehyde chromiumtricarbonyl complex , 1995 .

[10]  A. Alexakis,et al.  Determination of enantiomeric purity of hydroxy biaryls using 1H and 31P NMR on their diazaphospholidine derivatives , 1994 .

[11]  A. Alexakis,et al.  Chiral Diamines for a New Protocol To Determine the Enantiomeric Composition of Alcohols, Thiols, and Amines by 31P, 1H, 13C, and 19F NMR , 1994 .

[12]  A. Alexakis,et al.  Preparation and Utilization of Chiral Dihydropyridines. Synthesis of Chiral Indoloquinolizines and Benzoquinolizines , 1994 .

[13]  David J. Williams,et al.  Approaches to the assembly of the antifungal agent FR-900848: studies on the asymmetric synthesis of bicyclopropanes and an X-ray crystallographic analysis of (4R,5R)-2-[(1R,3S,4S,6R)-6-phenyl-1-bicyclopropyl]-1,3-dimethyl-4,5-diphenylimidazolidine , 1994 .

[14]  G. Rao,et al.  Novel reductive coupling of aldimines by indium under aqueous conditions , 1993 .

[15]  A. Alexakis,et al.  Resolution and asymmetric synthesis of ortho-substituted (benzaldehyde)tricarbonylchromium complexes , 1992 .

[16]  T. Shono,et al.  A novel method for stereoselective synthesis of (1R,2R)-diarylethylenediamines by reductive intramolecular coupling of aromatic diimines , 1992 .

[17]  A. Alexakis,et al.  Enantioselective synthesis of indoloquinolizidines , 1991 .

[18]  T. Sakurai,et al.  Diastereoselective cycloaddition of N-lithiated azomethine ylides to (E)-α,β-unsaturated esters bearing a C2-symmetric imidazolidine chiral controller , 1991 .

[19]  A. Alexakis,et al.  Chiral aminal templates 5. Preparation of chiral 3-carboxaldehydes-1,4-dihydropyridines , 1991 .

[20]  T. Imamoto,et al.  Samarium Diiodide-Promoted Reductive Coupling of Imines. , 1990 .

[21]  David C. Forbes,et al.  A Route to Vicinal Diamines from the Samarium(II) Iodide-Mediated Coupling of Aldimines , 1990 .

[22]  Shinji Tanaka,et al.  Reduction and Coupling Reaction of Imines Promoted by Ytterbium Metal , 1990 .

[23]  A. Alexakis,et al.  Chiral aminal templates 4. Chiral aryl metallic reagents: reactions with aldehydes☆ , 1990 .

[24]  A. Alexakis,et al.  Chiral aminal templates 3 diastereoselectivity of organometallic attack on aldehydes bearing a chiral imidazolidine group , 1990 .

[25]  J. Lellouche,et al.  Synthesis and reactivity of chiral organometallic phosphonium salts , 1990 .

[26]  A. Alexakis,et al.  Stereochemical effects of trimethylsilyl chloride (TMSCl) on the conjugate addition of organocopper reagents , 1990 .

[27]  S. Buchwald,et al.  Zirconocene complexes of imines. General synthesis, structure, reactivity, and in situ generation to prepare geometrically pure allylic amines , 1989 .

[28]  A. Alexakis,et al.  Chiral trifluoro diamines as convenient reagents for determining the enantiomeric purity of aldehydes by use of fluorine-19 NMR spectroscopy , 1989 .

[29]  A. Alexakis,et al.  Diastereoselective conjugate addition with acetals, oxazolidines and imidazolidines as chiral auxiliaries , 1988 .

[30]  H. Fujita,et al.  Reductive dimerization of imines in a Pb/Al bimetal redox system , 1988 .

[31]  A. Alexakis,et al.  Resolution and determination of enantiomeric excesses of chiral aldehydes via chiral imidazolidines , 1988 .

[32]  A. Alexakis,et al.  Titanium Induced Coupling of Imines to Symmetrical Vicinal (R*,R*)-Diamines , 1988 .

[33]  D. Seebach,et al.  Aminierende reduktive Kupplung aromatischer Aldehyde mit niervalenten Titan‐Reagenzien zu 1,2‐Diarylethylendiaminen , 1987 .

[34]  S. F. Pedersen,et al.  Convenient routes to vicinal diamines. Coupling of nitriles or N-(trimethylsilyl) imines promoted by NbCl4(THF)2 , 1987 .

[35]  T. Boettger,et al.  A Cautionary Note Regarding the Reductive Dimerization of Schiff Bases by Zinc Dust , 1981 .

[36]  Amin A. Siddiqui,et al.  Reduction of Schiff's Bases and Phenylhydrazones by Zinc Dust , 1980 .

[37]  M. Fiorini,et al.  Aminophosphine—Rhodium complexes as catalysts in asymmetric hydrogenation. The dependence of the enantioselectivity on the structure of the chiral ligands , 1979 .

[38]  W. Neumann,et al.  Synthesen mit Verbindungen R3M ? Hg ? MR3, XVI: (Silylamino)methylradikale und ihre Dimeren , 1978 .

[39]  James G. Smith,et al.  Reductive dimerization of Schiff bases by alkali metals. Isomerization of the dimeric dianions , 1972 .

[40]  J. Nosek Eine Modifikation der Frankland-Reaction IV. Einwirkung von aktiviertem Zink auf organische Verbindungen mit einer Carbonyl-, Imino- und Nitrogruppe , 1967 .

[41]  James G. Smith,et al.  THE REDUCTIVE DIMERIZATION OF N-BENZYLIDENE ANILINE , 1966 .

[42]  J. Eisch,et al.  Stereochemistry of the Bimolecular Metal Reduction of Benzalaniline1 , 1966 .

[43]  K. Bauer,et al.  [Reduction of benzylidene-alkylamines with activated aluminum in alcoholic solution]. , 1958, Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft.

[44]  R. Jaunin Sur le dianilino-1, 2-diphényl-1, 2-éthane. Séparation de diastéréoisomères sous forme de complexes avec la diméthylformamide , 1956 .

[45]  Werner Stühmer,et al.  Diastereomere N,N′‐substituierte 1,2‐Diphenyl‐äthylendiamine , 1953 .

[46]  W. Bachmann THE REDUCTION OF BENZALANILINE, BENZOPHENONE-ANIL AND BENZIL-ANIL BY THE SYSTEM MAGNESIUM + MAGNESIUM IODIDE , 1931 .

[47]  W. Schlenk,et al.  Forschungen auf dem Gebiete der alkaliorganischen Verbindungen. I. Über Produkte der Addition von Alkalimetal an mehrfache Kohlenstoff-Kohlenstoff-Bindungen , 1928 .

[48]  W. Schlenk,et al.  Über Metalladditionen an mehrfache Bindungen , 1914 .