32426-79-2

Upstream product

• 32426-80-5 (Z)-((prop-1-en-1-yloxy)methyl)benzene 
• 55775-43-4 2-Chloro-3,4-epoxy-4-phenylbutane 
• 14593-43-2 benzyl allyl ether 
• 4426-63-5 3,4-Epoxy-4-phenylbutan-2-ol 
• 23556-91-4 1-((1-(benzyloxy)propoxy)methyl)benzene 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 13807-91-5 benzyloxy-2-propanol 

Downstream Products

• 52755-39-2 (2E)-1-phenylbut-2-en-1-ol 
• 2032-33-9 N-benzyl-N-propylamine 
• 99398-32-0 trans,trans,cis-2-phenyl-3,5-dimethyl-4-(benzyloxy)piperidine 

Relevant academic research and scientific papers

Novel Synthesis of Enol Ethers from β-Alkoxy Alcohols through t-BuOK-Promoted Elimination Reaction

A new synthesis of enol ethers from β-alkoxy alcohols was achieved through a t-BuOK-promoted elimination reaction.

A highly Z-selective isomerization (double-bond migration) procedure for Allyl acetals and Allyl ethers mediated by Nickel complexes

A novel procedure for a highly Z-selective isomerization (double-bond migration) of acyclic allyl acetals and allyl ethers based on NiCl2dppb catalysis by activation with SuperHydride (lithium triethylborohydride) is described. The stereochemical outcome is compared with the results obtained with Ru and Rh catalysts. The applicability of the new process is demonstrated in the stereoselective synthesis of Claisen substrates (allyl vinyl ethers) from diallyl ethers.

Ruthenium(IV)-catalyzed isomerization of the C=C bond of O-allylic substrates: A theoretical and experimental study

A general mechanism to rationalize RuIV-catalyzed isomerization of the C=C bond in O-allylic substrates is proposed. Calculations supporting the proposed mechanism were performed at the MPWB1K/6-311+G(d,p)+SDD level of theory. All experimental observations in different solvents (water and THF) and under different pH conditions (neutral and basic) can be interpreted in terms of the new mechanism. Theoretical analysis of the transformation from precatalyst to catalyst led to structural identification of the active species in different media. The experimentally observed induction period is related to the magnitudes of the energy barriers computed for that process. The theoretical energy profile for the catalytic cycle requires application of relatively high temperatures, as is experimentally observed. Participation of a water molecule in the reaction coordinate is mechanistically essential when the reaction is carried out in aqueous medium.

(E) Enol ethers from the stereoselective reduction of α-alkoxy- β-ketophosphonates and Wittig type reaction

When α-alkoxy-β-ketophosphonates, prepared by the Rh(II) mediated insertion reaction of α-diazo-β-ketophosphonates into the OH bond of primary alcohols, were reduced either by NaBH4 in the presence of CaCl2 or by DIBAL, they respectively gave the corresponding anti or syn stereomeric hydroxyphosphonates with pronounced to complete stereoselectivity. Submitted to the action of potassium tert-butoxyde, syn isomers led to the corresponding pure (E) enol ethers in moderate to good yields. Under the same conditions anti isomers led to a mixture of (Z) and (E) enol ethers in rather poor yields. The sequence was applied to the preparation of some allyl-vinyl ethers with a (E) configuration for the vinylic double bond.

Encapsulated molecular catalysts in polysiloxane gels: Ruthenium cluster-catalyzed isomerization of alkenes

Novel ruthenium-encapsulating polysiloxane gels are prepared by treatment of polymethylhydrosiloxane with diols in the presence of (μ3, η2,η3,η5-acenaphthylene)Ru 3(CO)7, and act as reusable catalysts in the isomerization of alkenes without leakage of the catalyst species. The Royal Society of Chemistry.

Synthesis of tert-alkyl amino hydroxy carboxylic esters via an intermodular ene-type reaction of oxazolones and enol ethers

terf-Alkyl amino hydroxy carboxylic acids are abundantly present within the structure of many biologically active natural products. We describe herein the synthesis of these substrates using an oxazolone-mediated ene-type reaction with enol ethers followed by NaBH4 reduction of the intermediate oxazolone.

Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles

A pure ruthenium hydride complex with N-heterocyclic carbene (NHC) ligand was efficiently generated from the reaction of a second-generation Grubbs ruthenium catalyst with vinyloxytrimethylsilane and unambiguously characterized. This ruthenium hydride complex showed high catalytic activity for the selective isomerization of terminal olefin and for the cycloisomerization of 1,6-dienes. These reactions of N-allyl-o-vinylaniline lead to novel synthetic methods for heterocycles such as indoles and 3-methylene-2,3-dihydroindoles, which are useful synthons for bioactive natural products. These procedures address an important issue in diversity-oriented synthesis.

Synthesis, characterization, and reactivity of half-sandwich Ru(II) complexes containing phosphine, arsine, stibine, and bismutine ligands

The synthesis and some reactions of the Ru(II) and Ru(IV) half-sandwich complexes [RuCp(EPh3)(CH3CN)2]+ (E = P, As, Sb Bi) and when the former is weaker, that is in going down the series. Thus in the case of Bi,

A concise synthesis of carpanone using solid-supported reagents and scavengers

The synthesis of the natural product carpanone by utilization of polymer supported reagents, eliminating the need for conventional purification techniques was reported. The synthesis and crystal structure of a polymer-supported iridium catalyst for isomerization was also reported. The observations showed that isomerization of electron-rich aromatic compounds by the catalyst resulted in products with predominantly trans alkene geometry. However, the electron-poor derivatives were found to be less prone to rearrangement.

Selective isomerization of a terminal olefin catalyzed by a ruthenium complex: The synthesis of indoles through ring-closing metathesis

Aruthenium complex, generated from the Grubbs carbene catalyst with vinyloxytrimethylsilane, catalyzed the isomerization of terminal alkenes RCH2-CH=CH2 to internal alkenes RCH=CH-CH3. Application of this olefin isomerization to 2-(N-allylamino)styrene gave the corresponding enamines, which were converted into indoles by a standard ring-closing metathesis, see scheme (Ts = tosyl).