450406-75-4

Upstream product

• 3453-00-7 diethyl benzoylmethylphosphonate 
• 72019-14-8 (2-hydroxy-2-phenyl-ethyl)-phosphonic acid diethyl ester 
• 98-88-4 benzoyl chloride 
• 393-52-2 2-Fluorobenzoyl chloride 

Downstream Products

• 180906-56-3 diethyl (2S)-β-amino-β-phenylethylphosphonate 
• 827320-92-3 diethyl (2R)-β-amino-β-phenylethylphosphonate 

Relevant academic research and scientific papers

Enantioselective reduction of ketophosphonates using adducts of chiral natural acids with sodium borohydride

A method for asymmetric reduction of α- and β-ketophosphonates using chiral complexes prepared from sodium borohydride and natural aminoacids or tartaric acids was developed. Reduction of α or β-ketophosphonates by these reagents led to formation of chiral (S)- or (R)- hydroxyphosphonates. Reduction of chiral di-(1R,2S,5R)-menthylketophosphonates by the chiral complexes NaBH4/(R,R)-proline or NaBH4/(R,R)-tartaric acid due to the double matched asymmetric induction resulted in increased stereoselectivity of the reaction and led to the formation of hydroxyphosphonates up to 90% ee or higher. Dimenthyl 2-hydroxy-3- chloropropylphosphonate was utilized as a chiron for the preparation of a number of biologically active compounds in multigram quantity. ARKAT-USA, Inc.

Enantioselective hydrogenation of β-ketophosphonates with chiral Ru(II) catalysts

Highly effective asymmetric hydrogenation of β-ketophosphonates in the presence of Ru-(S)-SunPhos as catalyst was realized; good to excellent enantioselectivities (up to 99.9% ee) and excellent diastereoselectivities (96:4) were obtained.

Nonenzymatic kinetic resolution of racemic β-hydroxyalkanephosphonates with a chiral copper catalyst

Kinetic resolution of β-hydroxyalkanephosphonates was efficiently performed by 2-fluorobenzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with good s value of up to 21.

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 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.

Candida rugosa lipase-catalyzed enantioselective hydrolysis in organic solvents. Convenient preparation of optically pure 2-hydroxy-2-arylethanephosphonates

A convenient enzymatic method is presented for the preparation of optically pure 2-hydroxy-2-arylethanephosphonates. It is proved that 2-butyryloxy-2-arylethanephosphonates can be enantioselectively hydrolyzed in diisopropyl ether equilibrated with water