177468-91-6

Basic information

• Product Name: Propanedioic acid, [(2E)-1,3-diphenyl-2-propenyl]-, dimethyl ester
• CAS NO: 177468-91-6
• Molecular Formula: C20H20O4
• Molecular Weight: 324.376
• Mol File: 177468-91-6.mol
• Article Data: 83

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, [(2E)-1,3-diphenyl-2-propenyl]-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, [(2E)-1,3-diphenyl-2-propenyl]-, dimethyl ester(177468-91-6)
• EPA Substance Registry System: Propanedioic acid, [(2E)-1,3-diphenyl-2-propenyl]-, dimethyl ester(177468-91-6)

Safety Data

• Hazardous Substances Data: 177468-91-6(Hazardous Substances Data)

Upstream product

• 62668-02-4 (E)-1,3-diphenyl-2-propen-1-ol 
• 591-50-4 iodobenzene 
• 7318-33-4 cinnamaldehyde tosylhydrazone 
• 18424-76-5 sodiodimethylmalonate 
• 73930-97-9 3-acetoxy-1,3-diphenylpropene 
• 108-59-8 malonic acid dimethyl ester 
• 14371-10-9 (E)-3-phenylpropenal 
• 121440-73-1 carbonic acid 1,1-dimethylethyl 1,3-phenyl-2(E)-propenyl ester 
• 121440-72-0 (E)-1,3-diphenylallyl methyl carbonate 
• 18424-76-5 dimethyl malonate sodium salt 
• 87751-69-7 rac-(E)-1,3-diphenyl-3-acetoxy-prop-1-ene 
• 66684-74-0 dimethyl (E)-cinnamylidenemalonate 
• 95071-02-6 dimethyl 2-[(E)-(S)-1,3-diphenylallyl]-malonate 
• 121440-71-9 ethyl (E)-1,3-diphenyl-2-propen-1-yl carbonate 

Downstream Products

• 1159991-76-0 (4E)-3,5-diphenylpent-4-enoic acid 

Relevant articles and documents

Asymmetric allylic alkylation catalyzed by palladium complexes with new chiral ligands

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Ligand's electronegativity controls the sense of enantioselectivity in BIFOP-X palladium-catalyzed allylic alkylations

Palladium-catalyzed allylic alkylations of sodium dimethyl malonate with 1,3-diphenylallyl acetate, employing BIFOP-H (biphenylbisfencholphosphite) and analogue (i.e. BIFOP-X, X = D, Cl, CN, N3) ligands, all yield (S)-enantiomeric products, while alkylations to cyclohexenyl acetate yield the (R)-enantiomeric C-C coupling product (up to 91% yield, 70% ee). The fluoro derivative BIFOP-F however, "switches" the sense of enantioselectivity, yielding the (R)-enantiomer for 1,3-diphenylallyl acetate and the (S)-enantiomer for the cyclohexenyl acetate (up to 92% yield, 67% ee). Computational analyses of transition structures (M06-2X-D3/def2-TZVP//B3LYP-D3(BJ)/def2-SVP) for these Pd-catalyzed allylic alkylations reproduce the experimental preference of BIFOP-H (and analogue BIFOP-X ligands) for (R)- or (S)-enantiomeric products of 1,3-diphenylallyl or cyclohexenyl acetate, respectively. The "F-switch" of the sense of enantioselectivity from BIFOP-H to BIFOP-F is also apparent computationally and is found (NBO-analyses) to originate from lp(Pd) → σ?(P-O) or lp(Pd) → σ?(P-F) hyperconjugations. The higher electronegativity of F vs. H in BIFOP-X hence controls the sense of enantioselectivity of this Pd-catalyzed allylic alkylation.