476358-99-3

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 79-22-1 methyl chloroformate 
• 868-85-9 Dimethyl phosphite 
• 252574-53-1 (2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate 
• 100-42-5 styrene 
• 180294-79-5 dimethyl [1-(methoxycarbonyloxy)-2-propenyl] phosphonate 
• 162681-26-7 (R)-(+)-(1-Hydroxy-3-phenyl-2E-propenyl)phosphonic acid dimethyl ester 

Relevant academic research and scientific papers

A Practical and Scalable Synthesis of (S)- and (R)-1-(Dimethoxyphosphoryl)allyl Methyl Carbonates

The preparation of (S)- and (R)-1-(dimethoxyphosphoryl)allyl methyl carbonates is achieved on multigram scale from commercially available dimethyl phosphite and acrolein in three steps. The key steps involve an asymmetric Pudovik reaction and enzyme-catal

Palladium catalyzed additions to allylic hydroxy phosphonates: Applications in the enantioselective synthesis of enterolactone and turmerone

Reaction of nonracemic allylic hydroxy phosphonates, prepared by the asymmetric phosphonylation of unsaturated aldehydes, with methyl chloroformate in pyridine yields the corresponding carbonates. The carbonates are excellent substrates for the palladium-

Enantioseparation of α-Hydroxyallylphosphonates and Phosphonoallylic Carbonate Derivatives on Chiral Stationary Phases Using Sequential UV, Polarimetric, and Refractive Index Detection

Chromatographic separation of the enantiomers of parent compounds dimethyl α-hydroxyallyl phosphonate 1a and 1-(dimethoxyphosphoryl) allyl methyl carbonate 1b was demonstrated by high-performance liquid chromatography (HPLC) using Chiralpak AS-H and ad-H chiral stationary phases (CSP), respectively, using a combination of UV, polarimetric, and refractive index detectors. A comparison was made of the separation efficiency and elution order of enantiomeric α-hydroxyallyl phosphonates and their carbonate derivatives on commercially available polysaccharide AS, ad, OD, IC-3, and Whelk-O 1 CSPs. In general, the α-hydroxyallyl phosphonates were resolved on the AS-H CSP, whereas the carbonate derivatives 1b and 2b were preferentially resolved on the ad-H CSP. The impact of aryl substitution on the resolution of analytes 1d, 1e, 1f and 2, 3, 4, 5, 6, 7, 8 was evaluated. Thermodynamic parameters determined for enantioselective adsorption hydroxyphosphonates 1a and 4 on the AS-H CSP and carbonate 1b on the ad-H CSP demonstrated enthalpic control for separation of the enantiomers. Chirality 28:656–662, 2016.

Synthesis of cyclopentenones via intramolecular HWE and the palladium-catalyzed reactions of allylic hydroxy phosphonate derivatives

(Chemical Equation Presented) Palladium-catalyzed decarboxylative rearrangement of nonracemic phosphono allylic acetoacetates, or the intermolecular allylic substitution of nonracemic phosphono allylic carbonates with tert-butyl acetoacetate followed by h

Stereospecific Pd(O)-Catalyzed Malonate Additions to Allylic Hydroxy Phosphonate Derivatives: A Formal Synthesis of (-)-Enterolactone

A combination of cross-metathesis and malonate addition was applied to a formal synthesis of the mammalian lignan enterolactone 5. The cross-metathesis of alkene 6 and phosphonate 3a gave the substituted allylic phosphonate 3d. The palladium-catalyzed add