314249-68-8

Basic information

• Product Name: 1S,2S-bis[(1S)-1-phenylethyl]-1,2-diphenyl-1,2-EthanediaMine
• Synonyms: 1S,2S-bis[(1S)-1-phenylethyl]-1,2-diphenyl-1,2-EthanediaMine
• CAS NO: 314249-68-8
• Molecular Formula: C30H32N2
• Molecular Weight: 420.58848
• Mol File: 314249-68-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1S,2S-bis[(1S)-1-phenylethyl]-1,2-diphenyl-1,2-EthanediaMine(CAS DataBase Reference)
• NIST Chemistry Reference: 1S,2S-bis[(1S)-1-phenylethyl]-1,2-diphenyl-1,2-EthanediaMine(314249-68-8)
• EPA Substance Registry System: 1S,2S-bis[(1S)-1-phenylethyl]-1,2-diphenyl-1,2-EthanediaMine(314249-68-8)

Safety Data

• Hazardous Substances Data: 314249-68-8(Hazardous Substances Data)

Usage

Common Uses

As a ligand in asymmetric synthesis and catalysis.

Type of Compound

Organic compound.

Molecular Structure

Consists of two phenylethyl groups and two phenyl groups linked to a central ethylenediamine backbone.

Chiral Center

Present, which gives it stereochemical properties beneficial for catalytic reactions and enantioselective synthesis.

Application

Utilized in various chemical reactions to produce enantiomerically pure compounds.

Unique Value

Its unique structure and properties make it a valuable tool in the field of organic chemistry.

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 100-59-4 phenylmagnesium chloride 
• 129171-89-7 1,4-bis<(R)-α-methylbenzyl>-1,4-diaza-1,3-butadiene 
• 98393-39-6 (E)-N-benzylidene-α-methylbenzylamine 
• 591-51-5 phenyllithium 
• 280142-38-3 (4R,5R)-N,N'-bis[(1S)-1-phenylethyl]-3,6-divinyl-1,7-octadiene-4,5-diamine 
• 3129-98-4 (R)-benzylidene-(1-phenylethyl)amine 
• 56941-77-6 (R)-1-phenylethyl(benzylidene)amine 
• 90580-93-1 N,N'-bis<(R)-1-phenylethyl>-1,2-ethanediimine 

Relevant articles and documents

Design, development, and scale-up of a selective meso-epoxide desymmetrization process

A pilot-plant scale desymmetrization of the cyclic meso-epoxide 4b, using a chiral lithium amide prepared from symmetrical diamine 17, was designed and implemented to provide allylic alcohol 3b in high yield and greater than 99% ee. This chiral alcohol was converted to ketone 2b, a key intermediate in a new asymmetric synthesis of LY459477. Chiral diamine 17 was prepared from a readily available chiral precursor, (R)-α-methylbenzylamine, and could be recovered from the reaction mixture and reused. Studies performed to probe the mechanism of the rearrangement reaction of epoxide 4b showed that diamine 17 provided an optimal combination of selectivity and scaleability for this process.

Use of diamines containing the α-phenylethyl group as chiral ligands in the asymmetric hydrosilylation of prochiral ketones

Chiral diamines 1-7 were used in the enantioselective hydrosilylation of prochiral aromatic and aliphatic ketones. Some of these ligands combine chiral backbones and chiral N,N′-α-phenylethyl substituents that give rise to synergistic effects between these two groups and lead to catalysts that exhibit high enantioselectivity.

Synthesis of enantiomerically pure C2-symmetric acyclic and cyclic 1,2-diamines via pinacol coupling of imines

The inter- and intramolecular coupling of imines promoted by samarium diiodide and Lewis acids or by Zn/MsOH was extensively studied. The intramolecular reaction of chiral, enantiomerically pure bis-imines was also considered, and allowed the efficient, s

Rearrangement and substitution of pentadienyl groups in homopentadienylamines on treatment with organolithium reagents

(4R,5R)-N,N′-Bis[(1S)-1-phenylethyl]-3,6-divinyl-1,7-octadiene-4,5- diamine underwent rearrangement and/or substitution of one/two pentadienyl groups on treatment with 2-4 equiv. of an organolithium reagent (nBuLi, PhLi) in THF. By careful choice of experimental conditions, C1- or C2-symmetric 1,2-disubstituted 1,2-diamines could generally be obtained with good stereocontrol. It is proposed that the reaction proceeds through competitive pathways involving a 1,3-shift of the branched homopentadienyllithium amide moiety with retention of configuration and retro-pentadienyllithiation to form an intermediate imine. In contrast, only rearrangement was observed on treatment of (1R,S)-N-[(1S)-1-phenylethyl]-1-(2-pyridyl)-2-vinyl-3-butenylamine with 2 equiv. of nBuLi at -78 °C.

Synthesis of chiral C2-symmetric 1,2-diamines by the addition of organolithium reagents to N,N'-bis[(S)-1-phenylethyl]ethanediimine

The additions of alkyl-, phenyl- and vinyllithium reagents to N,N'-bis[(S)-1-phenylethyl]ethanediimine in THF at -78°C and in DME at -60°C gave high yields of 1,2-diamines with low stereocontrol. Care was taken to quench the reaction mixtures with de-aera

Samarium-promoted diastereoselective reductive coupling of optically active imines

The intermolecular pinacol-like coupling of optically active imines was performed stereoselectively with metallic samarium and a catalytic amount of iodine to give chiral C2-2,2'-ethylenediimino-diethanol derivatives.

Diastereoselective synthesis of 1,2-diphenyl-1,2-diaminoethanes by Yb(OTf)3 accelerated reductive coupling of imines

New reaction protocols have been established to perform the reductive coupling of N-benzyl benzaldimines to 1,2-diphenyl-1,2-diaminoethanes in mild, stereoselective, and catalytic conditions by the use of SmI2 and Yb(OTf)3.

Organic reaction in water. Part 1. A convenient method for reduction of imines using zinc powder

Reduction of imines was performed with zinc powder in 5% aqNaOH solution without any organic solvents under mild conditions, and the corresponding amines were obtained in good yields.

Simple Synthesis of a C2 Symmetric Vicinal Diamine: Highly Diastereoselective Grignard Addition toa Chiral Bis-Imine

The reaction of the enantiomerically pure bis-imine derived from glyoxal and (R)-α-methylbenzylamine with PhMgCl in diethylether is highly diastereoselective , resulting in the selective formation of the C2 symmetric vicinal diamine 7.