2403-38-5

Usage

Chirality

Chiral compound

Backbone

1,2-ethanediamine

Attached groups

Two butyl and two phenyl groups

Usage

a. Chelating agent in organic synthesis
b. Production of pharmaceuticals
c. Production of pesticides
d. Production of rubber additives

Coordination Complexes

Forms coordination complexes with metal ions

Industrial and Laboratory Applications

Useful in a variety of applications due to its ability to form coordination complexes

Chiral Nature

Important building block in the synthesis of enantiomerically pure compounds

Pharmaceutical Research and Development

Enantiomerically pure compounds are of particular interest in this field

Upstream product

• 2782-40-3 N-butylbenzamide 
• 1077-18-5 N-benzylidenebutan-1-amine 
• 100-52-7 benzaldehyde 
• 57527-55-6 (E)-N-benzylidenebutan-1-amine 
• 920-39-8 isopropylmagnesium bromide 

Relevant academic research and scientific papers

Direct reductive coupling of secondary amides: Chemoselective formation of vicinal diamines and vicinal amino alcohols

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

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

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

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.

Synthesis of Enantiomerically Pure 1,2-Diamines by Reductive Coupling of Tricarbony(benzaldimine)chromium Complexes

Enantiomerically pure 1,2-diamines are prepared by intermolecular pinacol coupling of planar chiral (benzaldimine)Cr(CO)3 complexes with samarium(II) diiodide.