171878-71-0

Basic information

• Product Name: (Sa)-2-chloro-dinaphthol[2,1-d:1',2'-f][1,2,3]dioxaphosphepine
• CAS NO: 171878-71-0
• Molecular Weight: 350.741
• Mol File: 171878-71-0.mol

Chemical Properties

• CAS DataBase Reference: (Sa)-2-chloro-dinaphthol[2,1-d:1',2'-f][1,2,3]dioxaphosphepine(CAS DataBase Reference)
• NIST Chemistry Reference: (Sa)-2-chloro-dinaphthol[2,1-d:1',2'-f][1,2,3]dioxaphosphepine(171878-71-0)
• EPA Substance Registry System: (Sa)-2-chloro-dinaphthol[2,1-d:1',2'-f][1,2,3]dioxaphosphepine(171878-71-0)

Safety Data

• Hazardous Substances Data: 171878-71-0(Hazardous Substances Data)

Upstream product

• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 602-09-5 1,1'-bi-2-naphthol 
• 18531-99-2 (S)-[1,1']-binaphthalenyl-2,2'-diol 

Downstream Products

• 171878-46-9 (racemic)-(1,1'-binaphthyl-2,2'-dioxy)PN(CHMe₂)PPh₂ 
• 688764-75-2 (R)-(1,1'-binaphthyl-2,2'-diyl)(5-(phenyl-2-yl)-10,15,20-tris(phenyl) zinc(II) porphyrin)phosphite 
• 1128108-45-1 (S)-(1,1'-binaphthyl-2,2'-diyl)(5-(phenyl-3-yl)-10,15,20-tris(phenyl) zinc(II) porphyrin)phosphite 
• 688764-15-0 (S)-(1,1'-binaphthyl-2,2'-diyl)(5-(phenyl-2-yl)-10,15,20-tris(phenyl) zinc(II) porphyrin)phosphite 
• 150646-49-4 4-Triphenylsilanyloxy-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 137156-23-1 4-(4-Methoxy-phenoxy)-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 
• 149917-85-1 (R,S)-binaphos 
• 921203-78-3 Mn(CO)2P(C₆H₅)3(C₅H₄CH₂OPO₂C₁₀H₆C₁₀H₆) 
• 1110685-33-0 rac-(1,1'-binaphthyl-2,2'-diyl)(2,4-di-tert-butylphenyl)phosphite 

Relevant articles and documents

Asymmetric hydroformylation catalysed by platinum complexes of new chiral bisphosphites

Asymmetric hydroformylation of styrene using bis(phosphite)PtCl2-SnCl2 systems gives branched aldehydes with high enantioselectivity (up to 91%).

Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization

The first total synthesis of the natural product impatien A is described. This concise synthesis features an aza-Heck cyclization to construct the complex spirocyclic ring system and provides a rare example of the use of aza-Heck cyclizations in complex molecule synthesis. To enable this key cyclization of an electrophilic nitrogen atom with a tetrasubstituted alkene, we utilized high-throughput experimentation to identify a new ligand and ultimately deliver impatien A in seven steps from known compounds.

Asymmetric Domino Heck/Dearomatization Reaction of β-Naphthols to Construct Indole-Terpenoid Frameworks

A palladium-catalyzed enantioselective Heck cyclization/dearomatization cascade via capturing the cyclized Heck π-allylpalladium intermediate by β-naphthols is reported, which provides a new strategy for the construction of chiral indole-terpenoid framewo

P-chirogenic diphosphazanes with axially chiral substituents and their use in rh-catalyzed asymmetric hydrogenation

A convenient synthesis of enantiopure P-chirogenic diphosphazanes incorporating bulky bisphenol and 1,1′-bi-2-naphtholderived substituents via the functionalization of a readily accessible enantiopure lithium phosphinoamide with chlorophosphoridites was developed. Since the product requires no subsequent deprotection, the protocol provides an easy, convenient synthesis of P-chirogenic ligands on the gram scale. The ligands were applied in the Rh-catalyzed asymmetric hydrogenation of benchmark substrates furnishing enantiomeric excess values up to 96%.

Rh(i)-Catalyzed enantioselective and scalable [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates

An asymmetric intermolecular [4 + 2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates, which was catalyzed by a rhodium(i)-chiral phosphoramidite complex, was developed. This protocol provided a highly enantioselective access to prepare carbonyl substituted cyclohexa-1,4-dienes with up to 96% yield and >99% ee. Notably, a cycloaddition on the 10 g scale gave the product in 92% yield and with 99% ee, which showed great potential for the scale-up synthesis of carbonyl substituted cyclohexa-1,4-dienes. In addition, oxidative aromatizations and hydrolysis of the products were also investigated.

ORGANOPHOSPHORUS COMPOUNDS, CATALYTIC SYSTEMS COMPRISING SAID COMPOUNDS AND METHOD OF HYDROCYANATION USING SAID CATALYTIC SYSTEMS

The present invention relates to organophosphorus compounds belonging to the phosphinite-phosphite family, catalytic systems comprising a metallic element forming a complex with said phosphinite-phosphite compounds and methods of hydrocyanation employed in the presence of said catalytic systems.

Palladium-catalyzed enantioselective allylic alkylations through C-H activation

A new ligand class: The title reaction was made possible by the discovery of a new class of phosphoramidite ligands. A variety of sterically and electronically diverse allylarenes undergo reaction with 2-acetyl-1-tetralones to form quaternary carbon stereocenters. This is a conceptually and mechanistically distinct strategy from traditional methods for the synthesis of enantioenriched allylic substitution products. 2,6-DMBQ=2,6- dimethylbenzoquinone. Copyright

Supramolecular control of selectivity in hydroformylation of vinyl arenes: Easy access to valuable β-aldehyde intermediates

Go against the flow! A rationally designed regioselective hydroformylation catalyst, [Rh/L], in which noncovalent ligand-substrate interactions allow the unprecedented reversal of selectivity from the typical α-aldehyde to the otherwise unfavored product β-aldehyde, is reported. This catalytic system opens up novel and sustainable synthetic pathways to important intermediates for the fine-chemicals industry.

Enantioselective allylic etherification: Selective coupling of two unactivated alcohols

An Ir(P,alkene) complex catalyzes the enantioselective allylic etherification of unactivated secondary allylic alcohols. Useful levels of enantioselectivity and yield were achieved with this operationally easy and robust protocol. Initial kinetic studies indicate a significant rate difference for the substrate enantiomers, allowing for a resolution process. cod=1,5-cyclooctadiene Copyright

A facile access to a novel bidentate enantiomerically pure P,N-donor ligand

The synthesis of a new chiral P,N-donor ligand containing a phosphite and a pyrazole site and its coordination chemistry with transition metals are described. The Royal Society of Chemistry 2009.