130696-26-3

Upstream product

• 186581-53-3 diazomethane 
• 184535-62-4 (S)-(1-phenylethyl)phosphonic acid 
• 4844-39-7 1-phenylvinylphosphonic acid dimethyl ester 
• 130696-14-9 (2R,6S)-2-Benzyl-3-tert-butyl-6-methyl-[1,3,2]oxazaphosphinane 2-oxide 
• 1499-19-0 benzylphosphonic dichloride 

Relevant academic research and scientific papers

Efficient asymmetric hydrogenation of α-acetamidocinnamates through a simple, readily available monodentate chiral H-phosphinate

An air-stable, simple (RP)-mentylbenzylphosphinate, readily available in large quantities, can efficiently induce the rhodium-catalyzed asymmetric hydrogenation of α-acetamidocinnamates with high enantioselectivity (up to 99.6 % ee). Intramolecular hydrogen bonding plays an important role in this asymmetric induction.

Impact on hydrogenation catalytic cycle of the R groups Cyclic feature in "r-SMS-Phos"

A series of R-SMS-Phos ligands was evaluated in the Rh(I)-catalyzed hydrogenation of a set of olefins showing a marked influence of the cyclic nature and structure of the R groups. Overall, cPen- and Cy-SMS-Phos performed efficiently, while Ph- and Bn-SMS-Phos exhibited slower kinetics and furnished lower ees also compared with C6F5CH2-SMS-Phos. The Rh(I)-(Cy-SMS-Phos) catalyst was screened under mild conditions displaying excellent enantioselectivities and high TOFs. Cases of catalysis under catalyst or substrate control were identified.

Diastereoselective alkylations of chiral, phosphorus-stabilized carbanions: N-alkyl substituent effects in P-alkyl-1,3,2-diazaphosphorinane 2-oxides

A systematic study of the diastereoselective alkylation of anions derived from racemic N-substituted P-alkyl 1,3,2,-diazaphosphorinane 2-oxides we carried out with variation of the N-substituent. High diastereoselectivity for the methylation of a P-benzyl

The asymmetric synthesis of α-substituted α-methyl and α-phenyl phosphonic acids: Design, carbanion geometry, reactivity and preparative aspects of chiral alkyl bicyclic phosphonamides

The design, preparation, structural and spectroscopic analyses of topologically unique and enantiomerically pure alkyl phosphonamides are described. In the case of α-ethyl and α-benzyl phosphonamides, the geometry of both the secondary and tertiary carbanions was determined to be planar through deprotonation/deuteration/alkylation experiments. Stereoselective alkylations of such systems proceeded in good yields and with high diastereoselectivities. The resulting α,α-alkylated phosphonamides were hydrolyzed to give the corresponding α,α-alkyl phosphonic acids with high degrees of enantiomeric purity.

Alkylations of chiral, phosphoryl- and thiophosphoryl-stabilized carbanions

A general method for the preparation of enantiomerically enriched phosphonic acids and phosphonates with three different α-substitution patterns (aryl, alkyl, and alkoxy) has been developed. Anions derived from enantiomerically enriched thiophosphonamidat

Stereoselective Alkylations of Chiral, Phosphorus-Stabilized Benzylic Carbanions

A series of 6-substituted 2-benzyl-3-tert-butyl-1,3,2-oxazaphosphorinanes was prepared in racemic and enantiomerically pure form.The diastereoselectivity of alkylation of the derived anions was examined as a function of ring substitution pattern, base, so