137386-72-2

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 367508-01-8 diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate 
• 448219-27-0 [(methoxy-methyl-carbamoyl)-methyl]-phosphonic acid bis-(2,2,2-trifluoro-ethyl) ester 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 55282-95-6 ethyl (2E)-5-phenylpent-2-enoate 

Downstream Products

• 33046-41-2 (E)-6-phenyl-3-hexen-2-one 

Relevant academic research and scientific papers

Stereoselective synthesis of either (E)- or (Z)-silyl enol ether from the same acyclic α,β-unsaturated ketone using cationic rhodium complex-catalyzed 1,4-hydrosilylation

The stereoselective synthesis of either (E)- or (Z)-silyl enol ether from the same acyclic α,β-unsaturated ketone is reported. Highly (Z)-selective conditions were the use of [Rh(cod)2]BF 4/DPPE at room temperature with no solvent, whereas (E)-selective conditions were the use of [Rh(cod)2]BF4/P(1-Nap) 3 (1-Nap = 1-naphthyl) under refluxing dichloromethane.

Application of organocerium reagents for the efficient conversion of Z-α,β-unsaturated Weinreb amides to Z-α,β-unsaturated ketones

The reactions of Z-rich unsaturated Weinreb amides with organolithium and organocerium reagents were examined. Taking in consideration both the extent of geometry retention and cleanness of the reaction, organocerium reagents were more effective for the conversion to Z-α,β-unsaturated ketones. Copyright

Synthesis of β-monosubstituted α,β-unsaturated amides with z-selectivity using diphenylphosphonoacetamides

The utility of diphenylphosphonoacetamides [(PhO)2P(O)CH 2CONRR′] as Horner-Wadsworth-Emmons reagents was examined with five different patterns of substitution upon the amide nitrogen atom (2a: R, R′ = CH2Ph; 2b: R = CH2Ph, R′ = H; 2c: R = Me, R′ = OMe; 2d: R, R′ = Ph; 2e: R, R′ = (CH2) 4). The reaction of 2a was found to be Z-selective for aromatic aldehydes with selectivities up to 95:5. Reagent 2b led to reasonable selectivity for both benzaldehyde (85:15) and 3-phenylpropionaldehyde (87:13), while 2c was somewhat effective for only the latter alkyl aldehyde (83:17). Compounds 2d and 2e exhibited slightly lower selectivities compared with 2a.