97852-37-4

Upstream product

• 132356-17-3 allyldiisobutyltelluronium bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 106-95-6 allyl bromide 
• 89110-81-6 diisobutyl telluronium allylide 
• 66713-38-0 1-allyl-tetrahydrothiophenium bromide 

Downstream Products

• 30448-78-3 p-methoxyphenylbutadiene 
• 123372-61-2 2-(4-methoxy-phenyl)-3-vinyl-thiirane 
• 668461-63-0 (2E)-N-benzhydryl-5-amino-5-cyclohexyloxycarbonyl-2-(4-methoxyphenyl)pent-2-enal 
• 668461-64-1 N-benzhydryl-5-(4-methoxyphenyl)-1,2,3,4-tetrahydro-pyridine-2-carboxylic acid cyclohexyl ester 

Relevant academic research and scientific papers

Synthesis of Highly Functionalized Allylic Alcohols from Vinyl Oxiranes and N-Tosylhydrazones via a Tsuji-Trost-Like palladium-Iodide Catalyzed Coupling

An unprecedented efficient palladium(0)-catalyzed reaction of vinyl oxiranes with N-tosylhydrazones, affording skipped allylic alcohols in total regioselectivity and stereoselectivity, with excellent functional-group compatibility, is reported. In this Tsuji-Trost-like allylation, we propose the use of N-tosylhydrazones as a synthetic equivalent of α-styryl anions. More than 20 new products are described, including naturally occurring derivatives. A catalytic system involving an iodide (I-) source is necessary to sustain the catalytic cycle.

Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis

Palladium-catalyzed allylic substitution, or "Tsuji-Trost"reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N-H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.

A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines

The diastereoselective synthesis of various substituted morpholines has been achieved from vinyloxiranes and amino-alcohols under sequential Pd(0)-catalyzed Tsuji-Trost/Fe(III)-catalyzed heterocyclization. Using the same strategy, 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines were obtained in good to excellent yields and diastereoselectivities.

Highly regioselective rearrangement of 2-substituted vinylepoxides catalyzed by gallium(III) triflate

Gallium(III) triflate catalyzed the rearrangement of 2-sub-stituted vinylepoxides into β,γ-unsaturated carbonyl compounds with high regio- and chemoselectivity (>97/3) in low catalyst loading (1-5 mol%). The alkyl-substituted trimethylsilylvinyl epoxides

New mechanistic aspects on the catalytic transformation of vinylthiiranes to mono and disubstituted 3,6-dihydro-1,2-dithiins by tungsten pentacarbonyl monoacetonitrile

Various alkyl and aryl mono- and disubstituted 3,6-dihydro-1,2-dithiins have been synthesised from their corresponding vinylthiiranes exploiting Adams' tungsten pentacarbonyl monoacetonitrile catalytic transformation. New conclusions pertaining to the rate determining step, the sensitivity of the process to precursor sterics and electronics, and the nature of various reaction intermediates are highlighted.

Chloroallyl Anion: Highly Regio- and Diastereoselective α-Addition of Chloroallyl Zinc Reagent to Carbonyl Compounds

The chloroallyl zinc reagent generated insitu by deprotonation of allyl chloride in the presence of lithium diisopropylamide and zinc chloride undergoes highly regio- and diastereoselective α-addition to carbonyl compounds to give syn chlorohydrins which

A Facile Synthesis of α,β-Unsaturated Epoxides via Allyldi-isobutyltelluronium Bromide

In the presence of solid KOH, allyldi-isobutyltelluronium bromide 2 reacts directly with aromatic aldehydes at room temperature under solid-liquid phase-transfer conditions to afford α,β-unsaturated epoxides 3 in excellent yields.

DIALKYLTELLURONIUM ALLYLIDE AS A NOVEL REAGENT FOR SYNTHESIS OF Α,Β-UNSATURATED EPOXIDES

Reaction of dialkyltelluronium allylide with aldehydes gave rise to α,β-unsatirated epoxides with moderate Z-selectivity and in good yields.