166734-94-7

Upstream product

• 31552-04-2 (Z)-1-phenyl-3-penten-1-yne 
• 31552-03-1 (Z/E)-(pent-3-en-1-ynyl)benzene 
• 536-74-3 phenylacetylene 

Downstream Products

• 27975-78-6 (S)-1-phenylpent-1-yn-3-ol 

Relevant academic research and scientific papers

An N-aryl-substituted oxazolidinone-containing ketone-catalyzed asymmetric epoxidation with hydrogen peroxide as the primary oxidant

(Chemical Equation Presented) Asymmetric epoxidation of various olefins with an N-aryl-substituted oxazolidinone-containing ketone as catalyst and hydrogen peroxide as the primary oxidant has been investigated, and up to 96% ee was obtained.

Titanium-salan-catalyzed asymmetric epoxidation with aqueous hydrogen peroxide as the oxidant

(Chemical Equation Presented) Keep it simple: A titanium complex with a salan ligand bearing phenyl groups at C3 and C3′ is an efficient catalyst for the enantioselective epoxidation of unfunctionalized olefins with aqueous hydrogen peroxide (see scheme); furthermore, the epoxidation was stereospecific. The C3 and C3′ substituents stabilize this complex and enhance the asymmetric induction.

Construction of pseudo-heterochiral and homochiral Di-μ- oxotitanium(Schiff base) dimers and enantioselective epoxidation using aqueous hydrogen peroxide

(Chemical Equation Presented) Salen's lot: Meerwein-Ponndorf-Verley reduction of [Ti(salen) (OiPr)2] (salen = bis(salicylidene) ethylenediaminato) complexes followed by treatment with water leads to the synthesis of pseudo-heterochiral and homochiral di-μ-oxotitanium dimers. These dimers, in particular (aR,S,Δ,aR,S,Δ)-dimer 1, efficiently catalyze the epoxidation of simple olefins using aqueous hydrogen peroxide (see scheme) with ee values up to 99% and turnover numbers up to 4600.

Biaryl-bridged salalen ligands and their application in titanium-catalyzed asymmetric epoxidation of olefins with aqueous H2O2

A series of biaryl-bridged salalen ligands together with their titanium complexes have been designed and synthesized. The Ti complexes could serve as highly efficient catalysts for the asymmetric epoxidation of a wide range of olefins, giving the corresponding epoxides with high ee values. A biaryl-bridged salalen titanium complex was developed and used in the enantioselective epoxidation of a range of olefins with aqueous hydrogen peroxide as the oxidant. Notably, the intramolecular dinuclear Ti catalyst possessing a biaryl bridge is highly efficient for the reaction, especially using terminal aromatic olefins as substrates.

Asymmetric counteranion-directed transition-metal catalysis: Enantioselective epoxidation of alkenes with Manganese(III) salen phosphate complexes

(Figure Presented) Figure Presentation Paired up: A highly active and enantioselective ion-pair epoxidation catalyst, consisting of an achiral Mn |||-salen complex and a chiral phosphate counteranion, mediates the epoxidization of a wide range of alkenes with high yields and enantioselectivities (see scheme). The unique role of the counteranion is to stabilize an enantiomorphic conformation of the cationic Mn catalyst.

Synthesis of metal-(pentadentate-salen) complexes: Asymmetric epoxidation with aqueous hydrogen peroxide and asymmetric cyclopropanation (salenH 2: N,N′-bis(salicylidene)ethylene-1,2-diamine)

It is known that the rates and stereochemical outcomes of epoxidations and cyclopropanations using a metallosalen (salenH2: N,N′- bis(salicylidene)ethylene-1,2-diamine) complex as catalyst are affected by a trans effect of the apical ligand of the complex. By taking into consideration this trans effect, we have synthesized optically active pentadentate salen ligands bearing an imidazole or pyridine derivative as the fifth coordinating group, and have prepared the corresponding manganese(III) and cobalt(II) complexes, in which the fifth ligand is expected to intramolecularly coordinate to the metal center and exert a trans effect. Indeed, high enantioselectivity has been achieved in epoxidations using aqueous hydrogen peroxide as the terminal oxidant and in cyclopropanations with these complexes as catalysts. In general, metallosalen-catalyzed reactions have been carried out in the presence of an excess of a donor ligand; however, the present reactions do not need the addition of any extra donor ligand.

Enantioselective epoxidation of conjugated cis-enynes by chiral dioxirane

(Chemical Equation Presented) This paper describes a highly chemo- and enantioselective epoxidation of conjugated cis-enynes using readily available glucose-derived ketone 2 as catalyst and Oxone as oxidant to form cis-propargyl epoxides in high ee's. The

PROCESS FOR PRODUCING OPTICALLY ACTIVE EPOXY COMPOUND, COMPLEX FOR USE IN THE PROCESS, AND PROCESS FOR PRODUCING THE SAME

There is provided a method for industrially producing optically active epoxy compounds by asymmetrically epoxidizing prochiral unsaturated compounds with an oxidant using as a catalyst a single substance or a di-μ-oxo dimer derived therefrom represented by any of the following formulae (I), (I'), (II), (II'), (III), (III'), (IV), and (IV'): [wherein R1s are independently an alkyl group or an aryl group; R2s are independently an alkyl group or an aryl group; R3s are independently an alkyl group or an aryl group, provided that two R3s may be bonded with each other to form a ring; R4s are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, or a cyano group; M is TiY2 (Y is Cl, alkoxide, or a μ-oxo ligand)].

Titanium-catalyzed asymmetric epoxidation of olefins with aqueous hydrogen peroxide: Remarkable effect of phosphate buffer on epoxide yield

The practicality of Ti(salan)-catalyzed asymmetric epoxidation was significantly improved by the addition of phosphate buffer (pH 7.4-8.0). Various olefins were transformed on a multigram scale into the corresponding epoxides with nearly complete product

Catalytic enantioselective epoxidation of unfunctionalized olefins: Utility of a Ti(Oi-Pr)4-salan-H2O2 system

Salan ligands bearing an ortho-substituted phenyl group at C3 and C3′ were found to serve as an effective auxiliary of a Ti(Oi-Pr) 4-salan-H2O2 system for enantioselective epoxidation. Simple olefins were converted into th