88753-35-9

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 6921-34-2 benzylmagnesium chloride 
• 100-44-7 benzyl chloride 
• 104-55-2 3-phenyl-propenal 
• 349611-37-6 [(2-pyridyldimethylsilyl)methyl]benzene 
• 591-50-4 iodobenzene 
• 108-88-3 toluene 
• 100-42-5 styrene 
• 122-78-1 phenylacetaldehyde 
• 6566-38-7 cis-1,2-dihydroxy-1,2-dimethyl-1,2-dihydroacenaphthalene 
• 100-39-0 benzyl bromide 
• 90766-67-9 1,1-dibromo-4-phenyl-1,3-butadiene 
• 38661-84-6 (E)-1,4-diphenylbut-1-en-3-one 
• 1608-03-3 (E)-but-1-en-3-yn-1-ylbenzene 

Downstream Products

• 297162-66-4 Malonic acid (E)-1-benzyl-3-phenyl-allyl ester ethyl ester 
• 38661-84-6 (E)-1,4-diphenylbut-1-en-3-one 
• 57767-03-0 1,4-diphenyl-2-methoxybut-3-ene 
• 1314801-91-6 (2E)-N-hydroxy-3-(1-((E)-1,4-diphenylbut-3-en-2-yl)-1H-1,2,3-triazol-4-yl)acrylamide 
• 1314802-30-6 (2E)-N-(4-methoxybenzyloxy)-3-(1-((E)-1,4-diphenylbut-3-en-2-yl)-1H-1,2,3-triazol-4-yl)acrylamide 
• 1314802-14-6 (E)-3-azido-1,4-diphenylbut-1-ene 

Relevant academic research and scientific papers

Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters

In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.

Br?nsted Acid Enabled Nickel-Catalyzed Hydroalkenylation of Aldehydes with Styrene and its Derivatives

A Br?nsted acid enabled nickel-catalyzed hydroalkenylation of aldehydes and styrene derivatives has been developed. The Br?nsted acid acts as a proton shuttle to transfer a proton from the alkene to the aldehyde, thereby leading to an economical and byproduct-free coupling. A series of synthetically useful allylic alcohols were obtained through one-step reactions from readily available styrene derivatives and aliphatic aldehydes in up to 88 % yield and with high linear selectivity.

Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents

Palladium-catalyzed conjunctive cross-coupling is used for the synthesis of enantioenriched allylboron reagents. This reaction employs nonsymmetric bis(alkenyl)borates as substrates and appears to occur by a mechanism that involves selective activation of the less substituted alkene followed by migration of the more substituted alkene during the course of a Pd-induced metalate rearrangement.

Nazarov cyclization of divinyl ketones bearing an ester group at the β-position: A remarkable effect of α-substitution and alkene geometry on regioselectivity

The Nazarov cyclization of divinyl ketones with an ester at the β-position was examined with particular reference to where the cyclic double bond forms. We observed unprecedented regioselectivity, dictated by the subtle substitution patterns at the α-position and alkene geometry of α,β and mostly, this selectivity is regardless of substitutions at α′- and β′-positions. The major implications of these observations are an aromatic group at the α-position with E-olefin geometry provides a cyclopentenone in which the double bond is not in conjugation with an ester, whereas Z-olefin provides a cyclopentenone in which the double bond is in conjugation with an ester; and divinyl ketones bearing an ester group at the β-position and an alkyl group at the α-position with E-olefin geometry provide a cyclopentenone in which the double bond is in conjugation with the ester.

Synthesis of highly decorated chiral 2-nitro-cyclohexane carboxylic esters through microwave-assisted organocatalyzed cascade reactions

Starting from (E)-β-substituted-β-nitroacrylates and α,β-unsaturated ketones, a stereoselective organocatalyzed one-pot methodology allowed to synthesize highly decorated chiral 2-nitro-cyclohexane carboxylic esters. The reaction is promoted by Cinchona a

Regioselective hydrations of 1-aryl-3-en-1-ynes using gold and platinum catalysts: Selective production of 2-en-1-ones and 3-en-1-ones

Regiocontrolled hydrations of 1-aryl-3-en-1-ynes have been accomplished with IPrAuOTf and PtCl2/CO to yield 3-en-1-ones and 2-en-1-ones efficiently; our experimental data indicates that the sizes of catalysts play an important role. This journa

Structure-based optimization of click-based histone deacetylase inhibitors

Previously, we reported a click-chemistry based approach to the synthesis of a novel class of histone deacetylase (HDAC) inhibitors [1]. The lead compound NSC746457 was found to be as potent as SAHA (Vorinostat). Further optimization of NSC746457 by using

Unusually accelerated silylmethyl transfer from tin in stille coupling: Implication of coordination-driven transmetalation

The palladium-catalyzed cross-coupling reaction of 2-PyMe2SiCH2SnBu3 with aryl iodide (Ar-I) exclusively produced the 2-PyMe2SiCH2 transferred product 2-PyMe2SiCH2Ar. The relative transfer ability of organic group from tin was found to be 2-PyMe2SiCH2 ? Ph > Me > Bu ? PhMe2SiCH2, which implies the beneficial pyridyl-to-palladium coordination effect. Thus, the transfer of the silylmethyl group from tin to palladium was remarkably accelerated by simply appending the 2-pyridyl group on silicon. The pyridyl-to-palladium coordination was validated in the palladium(II) complex 2-PyMe2SiCH2PdClPPh3 by 1H NMR and X-ray crystal structure analysis. The cross-coupling product was used for further transformations. The C - Si oxidation of the cross-coupling product 2-PyMe2SiCH2Ar afforded ArCH2OH in high yield. The fluoride ion-catalyzed 1,2-addition of 2-PyMe2SiCH2Ar to carbonyl compound (RR′C=O) gave ArCH2C(OH)RR′ in high yield.

Diastereoselectivity in the formation of bicyclic cyclopropane carboxylic acid lactones

The intramolecular cyclization of malonic acid allylic esters yields bicyclic cyclopropane carboxylic acid lactones in a phase transfer catalysed reaction. The substituents of the allylic moiety and the reaction temperature influence the diastereomeric composition of the products.