503538-68-9

Usage

Chemical Properties

White crystalline powder

Reactions

A chiral diphosphine ligand used in the highly-enantioselective hydrogenation of ketoesters, hydroxyketones, ketophosphonates and succinates. A ligand used for the dynamic kinetic resolution of α,β?unsaturated lactones via asymmetric copper-catalyzed conjugate reduction. Used in the intramolecular Heck reaction for the synthesis of diterpenoids. Used in asymmetric Pauson-Khand reaction. Used in asymmetric iminonitroso Diels-Alder reaction. Palladium catalyzed asymmetric hydrogenation of N-tosyl ketimines

Upstream product

• 503538-67-8 [2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis-(diphenylphosphane oxide) 
• 445380-61-0 (5-iodo-2,3-dihydro-1,4-benzodioxin-6-yl)diphenylphospane oxide 
• 503269-72-5 (2,3-dihydro-1,4-benzodioxin-6-yl)diphenylphosphine 
• 493-09-4 benzo-1,4-dioxane 
• 52287-51-1 6-bromo-1,4-benzodioxane 

Downstream Products

• 888955-60-0 hydrido(acetato)[(S)-(2,2',3,3'-tetrahydro(5,5'-bi-1,4-benzodioxin)-6,6'-diyl)bis(diphenylphosphine)]iodoiridium(III) 

Relevant academic research and scientific papers

Novel diphosphines, their complexes with transisition metals and their use in asymmetric synthesis

The invention relates to novel diphosphines, in optically pure or racemic form, of formula (I): in which: R1 and R2 are a (C5-C7)cycloalkyl group, an optionally substituted phenyl group or a 5-membered heteroaryl group; and A is (CH2—CH2) or CF2. The invention further relates to the use of a compound of formula (I) as a ligand for the preparation of a metal complex useful as a chiral catalyst in asymmetric catalysis, and to the chiral metal catalysts comprising at least one ligand of formula (I).

Synthesis and Molecular Modeling Studies of SYNPHOS(R), a New, Efficient Diphosphane Ligand For Ruthenium-Catalyzed Asymmetric Hydrogenation

A new, optically active, atropisomeric diphosphane ligand, (2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl)bis-(diphenylphosphane) (SYNPHOS(R)), has been synthesized, characterized, and used in ruthenium-catalyzed asymmetric hydrogenations. This new ligand has been compared with other atropisomeric diphosphanes (BINAP and MeO-BIPHEP) with respect to their dihedral angles calculated by molecular modeling and the enantioselectivity of their ruthenium-mediated hydrogenation reactions.

SYNPHOS, a new chiral diphosphine ligand: Synthesis, molecular modeling and application in asymmetric hydrogenation

A new optically active diphosphine ligand, [(5,6),(5′,6′)-bis(ethylenedioxy)biphenyl-2,2′-diyl]bis (diphenylphosphine) (SYNPHOS) has been synthesized and used in ruthenium-catalyzed asymmetric hydrogenation. This new ligand has been compared to other diphosphines (BINAP and MeO-BIPHEP), regarding their dihedral angles and the enantioselectivity in the ruthenium mediated hydrogenation reaction.

SYNPHOS: A new atropisomeric diphosphine ligand. From laboratory-scale synthesis to scale-up development

A new optically active diphosphine ligand, [(5,6),(5′,6′)-bis(ethylenedioxy)biphenyl.2,2′-diyl]bis (diphenylphosphine) (SYNPHOS) has been synthesized. Laboratory-scale synthesis and scale-up development of this ligand are described herein. This new atropisomeric diphosphine was also used in ruthenium-catalyzed asymmetric hydrogenation.