882992-52-1

Basic information

• Product Name: (R,S,S)-(-)-(2,6-diphenyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl) bis(1-phenylethyl)amine
• CAS NO: 882992-52-1
• Molecular Weight: 691.809
• Mol File: 882992-52-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R,S,S)-(-)-(2,6-diphenyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl) bis(1-phenylethyl)amine(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S,S)-(-)-(2,6-diphenyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl) bis(1-phenylethyl)amine(882992-52-1)
• EPA Substance Registry System: (R,S,S)-(-)-(2,6-diphenyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl) bis(1-phenylethyl)amine(882992-52-1)

Safety Data

• Hazardous Substances Data: 882992-52-1(Hazardous Substances Data)

Usage

General Description

The chemical (R,S,S)-(-)-(2,6-diphenyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl) bis(1-phenylethyl)amine, also known as P-Chiral diamine, is a complex organic compound. It is a chiral ligand that is used in asymmetric catalysis and organic synthesis. (R,S,S)-(-)-(2,6-diphenyl-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl) bis(1-phenylethyl)amine contains a phosphorus atom and two stereocenters, making it an important building block in the synthesis of chiral compounds. It has a wide range of applications in the pharmaceutical and agrochemical industries, and its unique structure and properties make it a valuable tool for the development of new chemical processes and products.

Upstream product

• 21003-56-5 (1S,1'S)-bis(1-phenylethyl)amine 
• 75640-70-9 (S)-3,3'-diphenyl-2,2'-dihydroxy-1,1'-binaphthyl 
• 40648-92-8 (R,R)-(+)-bis[alpha-methylbenzyl]amine hydrochloride 
• 75684-93-4 (R)-(+)-3,3'-diphenyl-[1,1'-binaphthalene]-2,2'-diol 
• 777067-26-2 [(R,R)-bis(α-methylbenzyl)amino]phosphorous dichloride 
• 10024-74-5 (R,R)-N,N-bis-(1-phenylethyl)amine 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 189518-78-3 (Ra)-3,3’-diiodo-2,2’-bis(methoxymethoxy)-1,1’-binaphthalene 

Relevant articles and documents

Asymmetric catalytic hydrogenolysis of aryl-halide bonds in fused arene chromium and ruthenium complexes

Access to highly enantioenriched planar chiral [Cr(5-bromonaphthalene)(CO) 3] (6), [Ru(η5-C5R5)(5- bromonaphthalene)][PF6] (42) and [Ru(η5-C 5R5)(4-bromoindene)] (44) was sought using asymmetric hydrogenolysis of [Cr(5,8-dibromonaphthalene)(CO)3] (5), [Ruη5-C5R5)(5,8-dibromonaphthalene)] (39) and [Ru(η5-C5R5)(4,7-dibromoindene)] (40), respectively. Initial efforts focused on the chromium complex 5. Pd0 catalysts with dimethoxyethane as the solvent and LiBH4 or NaBH 3CN as a hydride source worked best. Nineteen chiral bidentate phosphorus ligands were screened in this reaction. Asymmetric induction was low to modest with product ee's in the range of 4 to 52% and yields of 6 of up to 70 %. Chiral phosphoramidite ligands proved superior and a bulky ligand derived from a Whitesell amine and 3,3′-diphenyl-binaphtol afforded 6 with an ee of 97%. The high enantioselectivity is largely due to the initial desymmetrization reaction though kinetic resolution also plays an important role as shown by the determination of a selectivity factor s = 8.5 at -10°C. Initially high ligand loadings (4 equiv/Pd) were necessary to achieve good asymmetric induction. This could be traced to the trapping of the chiral ligand by borane formed in the reaction. Addition of 1,4-diazabicyclo[2.2.2]octane (DABCO) suppressed this, and its addition led to the use of Pd and chiral ligand in a 1:1.2 ratio. Asymmetric hydrogenolysis of cationic dibromonaphthalene and neutral dibromoindenyl complexes of Ru cyclopentadienyl complexes was investigated and afforded the following results : [RuCp(5-bromonaphthalene)]- [PF6] (39a; 75%, 90% ee), [RuCp*(5-bromonaphthalene)] [PF 6] (39 b; 88%, 99% ee), [RuCp(4-bromoindenyl)] (44a; 72%, 96% ee), and [RuCp*(4-bromoindenyl)] (44 b; 62%, 68% ee).

Asymmetric intramolecular hydroamination of allenes using mononuclear gold catalysts

The intramolecular gold-catalyzed asymmetric hydroamination of allenes was studied by screening a series of mononuclear gold(I) and -(III) complexes in combination with silver salts. Among the various chiral monophosphine and diaminocarbene ligands tried,

Gold-catalyzed [4C+2C] cycloadditions of allenedienes, including an enantioselective version with new phosphoramidite-based catalysts: Mechanistic aspects of the divergence between [4C+3C] and [4C+2C] pathways

Gold(I) complexes featuring electron acceptor ligands such as phosphites and phosphoramidites catalyze the [4C+2C] intramolecular cycloaddition of allenedienes. The reaction is chemo- and stereoselective, and provides trans-fused bicyclic cycloadducts in