1165-52-2Relevant academic research and scientific papers
Synthesis of Enantiomerically Pure 1,2-Diamines by Reductive Coupling of Tricarbony(benzaldimine)chromium Complexes
Taniguchi, Nobukazu,Uemura, Motokazu
, p. 51 - 53 (1997)
Enantiomerically pure 1,2-diamines are prepared by intermolecular pinacol coupling of planar chiral (benzaldimine)Cr(CO)3 complexes with samarium(II) diiodide.
Direct reductive coupling of secondary amides: Chemoselective formation of vicinal diamines and vicinal amino alcohols
Huang, Pei-Qiang,Lang, Qi-Wei,Wang, Ai-E,Zheng, Jian-Feng
supporting information, p. 1096 - 1099 (2015/02/19)
We report the first one-pot reductive homocoupling reaction of secondary amides and cross-coupling reaction of secondary amides with ketones to give secondary vicinal diamines and amino alcohols. This method relies on the direct generation of α-amino carb
Homocoupling of aldimines mediated by zirconocene: Synthesis of vicinal diamines and imidazolidines
Soueidan, Mohamad,Hélion, Florence,Namy, Jean-Louis,Szymoniak, Jan
scheme or table, p. 1348 - 1350 (2011/04/15)
The reductive coupling of imines in the presence of the lanthanide-originated zirconocene equivalent allows the synthesis of vicinal diamines or imidazolidines under mild conditions in good yields with high diastereoselectivity.
Reduction and reductive coupling of imines by Sm(II)-based reagents
Kim, Myeongseob,Knettle, Brian W.,Dahlén, Anders,Hilmersson, G?ran,Flowers II, Robert A.
, p. 10397 - 10402 (2007/10/03)
The reductive coupling of aldimines and ketimines by a series of Sm(II)-based reagents (SmI2, SmI2-HMPA, SmBr2, Sm{N[Si(CH3)3]2}2, and SmI 2/triethylamine/water) were examined. In general, aldimines and ketimines were efficiently reduced or coupled using reductants that are more powerful than SmI2, and the use of Sm{N[Si(CH3) 3]2}2 led to higher diastereoselectivities in reductive coupling reactions. Surprisingly, only the combination of SmI 2/triethylamine/water was capable of reducing and coupling para-substituted benzaldimines and coupling ketimines.
Stereoselective pinacol coupling of planar chiral (benzaldehyde)Cr(Co)3, (benzaldimine)Cr(CO)3, ferrocenecarboxaldehyde and (dienal)Fe(CO)3 complexes with samarium diiodide
Taniguchi, Nobukazu,Uemura, Motokazu
, p. 12775 - 12788 (2007/10/03)
An intermolecular pinacol coupling of the Planar chiral tricarbonylchromium complexes of o-substituted benzaldehydes or benzaldimines with samarium(II) diiodide in THF produces exclusively threo 1.2-diols or 1,2-diamines in an optically pure form, while the corresponding racemic o- substituted benzaldehyde or benzaldimine chromium complexes give a mixture of threo and erythro pinacol coupling products in a various ratio depending upon the nature of o-substituent. Similarly, planar chiral 2-substituted ferrocenecarboxaldehydes and (dienal)Fe(CO)3 produce the corresponding 1.2- diols with high stereoselectivity. The generated transition metal-complexed ketyl radical intermediates are configurationally stable with restriction to a rotation about C(α)-C(ipso) bond.
