311808-93-2

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 2236-01-3 acetonyltriphenylphosphonium bromide 
• 917-54-4 methyllithium 
• 489431-30-3 (Z)-N-methoxy-N-methyl-5-phenyl-2-pentenamide 
• 1092535-17-5 6-phenylhex-3-yn-2-one 
• 78-95-5 chloroacetone 
• 16520-62-0 4-Phenyl-1-butyne 
• 870776-73-1 (±)-6-phenylhex-3-yn-2-ol 

Relevant academic research and scientific papers

Polyethyleneimine-Supported Triphenylphosphine and Its Use as a Highly Loaded Bifunctional Polymeric Reagent in Chromatography-Free One-Pot Wittig Reactions

A polyethyleneimine-supported triphenylphosphine reagent has been synthesized and used as a highly loaded bifunctional homogeneous reagent in a range of one-pot Wittig reactions that afforded high yields of the desired products after simple purification procedures. The approach also served efficiently in tandem reaction sequences involving a one-pot Wittig reaction followed by conjugate reduction of the newly formed alkene product in situ. In these transformations, the phosphine oxide groups generated in the Wittig reaction served as the catalyst for activating trichlorosilane in the subsequent reduction reaction.

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Catalytic asymmetric hydroperoxidation of α,β-unsaturated ketones: An approach to enantiopure peroxyhemiketals, epoxides, and aldols

(Chemical Equation Presented) Efficient, selective: The primary amine salt 1 derived from quinine efficiently catalyzes the highly enantioselective hydroperoxidation of α,β-unsaturated ketones furnishing stable and isolable cyclic peroxyhemiketals in enan

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

The reaction of triphenylphosphonium or triphenylarsonium salts with aldehyde: Effect of the counteranion on their reactivity

Some acetonyltriphenylphosphonium, methoxycarbonylmethyltriphenylphosphonium salts and their triphenylarsonium analogues could undergo Wittig reaction with aldehyde in good yields. Their reactivity was counteranion-dependent and was arranged in the following order: p-TsO-, Br-3CO2/-2CO2/-2/-, HCO2/-, MeCO2/-. The proton-coupled 13C NMR splitting patterns of the α-methylene groups provided a valuable information to predict their reactivity with aldehyde. Only those onium salts without C-H coupling could undergo Wittig reaction. (C) 2000 Elsevier Science Ltd.