139566-47-5

Upstream product

• 3195-24-2 diallylmalonic acid diethyl ester 
• 2049-80-1 (2-propenyl)propanedioic acid diethyl ester 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 4392-24-9 Cinnamyl bromide 

Downstream Products

• 63082-55-3 diethyl (E)-cinnamyl malonate 
• 112391-52-3 5-phenyl-2-prop-2-enylpent-4-enoic acid 
• 1453416-56-2 (E)-2-allyl-5-phenyl-N-(p-tolyl)pent-4-enamide 
• 139566-50-0 (3S,4R)-3-Benzyl-4-formyl-cyclopentane-1,1-dicarboxylic acid diethyl ester 
• 139566-50-0 (3S,4S)-3-Benzyl-4-formyl-cyclopentane-1,1-dicarboxylic acid diethyl ester 
• 139566-50-0 3-Benzyl-4-formyl-cyclopentane-1,1-dicarboxylic acid diethyl ester 
• 112391-55-6 Toluene-4-sulfonic acid (E)-2-allyl-5-phenyl-pent-4-enyl ester 
• 112391-53-4 2-allyl-5-phenyl-4-penten-1-ol 
• 139566-28-2 3-Benzyl-4-dimethoxymethyl-cyclopentane-1,1-dicarboxylic acid diethyl ester 

Relevant academic research and scientific papers

Study on the total synthesis of velbanamine: Chemoselective dioxygenation of alkenes with PIFA via a stop-and-flow strategy

A "stop-and-flow" strategy was developed for the chemoselective dioxygenation of alkenes with a PIFA-initiated cyclization. This method is conceived for the desymmetrization of seco-diene, and a series of substituted 5-hydroxymethyl-γ-lactones were constructed after hydrolysis. This strategy also differentiates terminally substituted alkenes and constitutes a potentially novel synthetic approach for the efficient synthesis toward velbanamine.

Phosphoramidite ligands in iridium-catalyzed allvlic substitution

A new phosphoramidite ligand was used in the iridium-catalyzed allylic substitution reaction. This permitted high regio- and enantioselectivities on a wide variety of substrates and nucleophiles. Because of the stereospecificity of the reaction obtained by using branched substrates, a kinetic resolution reaction was attempted. The origin of the impressive efficiency of this ligand in terms of kinetics was explored in detail, as was the role of the substituent in the ortho-position of the amine moiety.

Catalytic deallylation of allyl- and diallylmalonates

Substituted allylmalonates undergo the selective C-C bond cleavage in the presence of triethylaluminum and a catalytic amount of nickel and ruthenium phosphine complexes, resulting in the loss of the allyl moiety and formation of monosubstituted malonates. Comparison of reactivity of the nickel and ruthenium complexes showed that the use of the former is general with respect to the structure of the substituted allylmalonates, and the activity of the latter depended on the substitution pattern of the double bond of the allylic moiety. The smooth deallylation may encourage the use of the allyl group as a protective group for the acidic hydrogen in malonates. Copyright