5750-22-1

Upstream product

• 103-80-0 phenylacetyl chloride 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 30018-16-7 (1-ethoxycarbonylethyl)triphenylphosphonium bromide 
• 6111-99-5 ethyl diazoalaninate 
• 536-74-3 phenylacetylene 
• 98-88-4 benzoyl chloride 

Downstream Products

• 126309-31-7 2-fluoro-2-methyl-4-phenylbut-3-ynoic acid ethyl ester 
• 1365534-63-9 ethyl 2-benzyl-2,3-dimethyl-4-phenyl-3(E)-butenoate 
• 2807-46-7 ethyl 2,2,3-trimethyl-4-phenyl-3(Z)-butenoate 
• 2807-47-8 ethyl 2,2,3-trimethyl-4-phenyl-3(E)-butenoate 
• 1365534-62-8 ethyl 2-(1'-hydroxy-1'-methylethyl)-2,3-dimethyl-4-phenyl-3(Z)-butenoate 
• 1365534-60-6 ethyl 2-methyl-3-(isopropyl)-4-phenyl-3(Z)-butenoate 
• 57496-47-6 2-methyl-4-phenyl-2,3-allenoic acid 
• 1062642-17-4 (4R,6S)-(+)-6-(ethoxycarbonyl)-3-ethyl-2,6-dimethyl-4-phenyl-5(Z)-benzylidenecyclohex-2-enone 
• 1062642-23-2 (4R,6S)-(+)-6-(ethoxycarbonyl)-2,3,6-trimethyl-4-phenyl-5(Z)-benzylidenecyclohex-2-enone 
• 1062642-26-5 (4R,6S)-(+)-3-butyl-6-(ethoxycarbonyl)-2,6-dimethyl-4-phenyl-5(Z)-benzylidene-cyclohex-2-enone 
• 1062642-16-3 (4S,6R)-(-)-6-(ethoxycarbonyl)-3-ethyl-2,6-dimethyl-4-phenyl-5(Z)-benzylidenecyclohex-2-enone 
• 1062642-20-9 (4S,6R)-(-)-6-(ethoxycarbonyl)-2,3,6-trimethyl-4-phenyl-5(Z)-benzylidenecyclohex-2-enone 
• 1062642-33-4 ethyl 3-ethyl-2-methyl-4-phenyl-3-butenoate 
• 1062642-24-3 (4S,6R)-(-)-3-butyl-6-(ethoxycarbonyl)-2,6-dimethyl-4-phenyl-5(Z)-benzylidene-cyclohex-2-enone 

Relevant academic research and scientific papers

Chiral Allenes via Alkynylogous Mukaiyama Aldol Reaction

Herein we describe the development of a catalytic enantioselective alkynylogous Mukaiyama aldol reaction. The reaction is catalyzed by a newly designed chiral disulfonimide and delivers chiral allenoates in high yields and with excellent regio-, diastereo

Enantioselective gold(I)-catalyzed intramolecular (4+3) cycloadditions of allenedienes

Allene-tethered dienes (1) undergo an intramolecular and highly enantioselective (4+3) cycloaddition when treated with suitable chiral phosphoramidite/gold(I) catalysts (see scheme; Ar=9-anthracenyl). The reactions provide synthetically relevant [5.3.0] and [5.4.0] fused bicyclic systems 2 with good yields, complete diastereocontrol, and excellent enantioselectivities.

Copper-catalyzed synthesis of 2,4-disubstituted allenoates from α-diazoesters

Chemical equations presented. A Cu-catalyzed method for coupling α-substituted-α-diazoesters with terminal alkynes to give substituted allenoates is described. Key to the development of a selective method was the recognition that an adventitous base catalyzes the isomerization to form the allenoate product. A plausible mechanism is proposed, based in part on evidence against a mechanism that involves a Cu(I)-acetylide as a low-valent intermediate.

Study on the selectivity in the electrophilic monofluorination of 2,3-allenoates with Selectfluor: An efficient synthesis of 4-fluoro-2(5H)-furanones and 3-fluoro-4-oxo-2(E)-alkenoates

Different from the reaction of 2,3-allenoic acids with Selectfluor, 4-fluoro-2(5H)-furanones and (E)-3-fluoro-4-oxo-2-alkenoates were highly selectively generated from 2,4-disubstituted 2,3-allenoates with Selectfluor under different conditions in moderate yields. The reaction of 2, 4, 4-trisubstituted 2,3-allenoates afforded the corresponding 4-fluoro-2(5H)-furanones highly selectively with up to 95% yield under different conditions. The scope of the substrates has been carefully explored. Due to the more readily availability of 2,3-allenoates as compared to 2,3-allenoic acids, new 4-fluoro-2(5H)furanones were prepared. Based on the isolation and characterization of the minor fluorohydroxylation product E-5m, a mechanism has been proposed. The Royal Society of Chemistry 2010.

Scope and limitations of palladium-catalyzed cross-coupling reactions with organogold compounds

Five different alkenylgold(I) phosphane complexes were prepared and then investigated in [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-catalyzed cross-coupling reactions with different aryl halides, heterocyclic halides, an alkenyl halide, an alkynyl halide, allylic substrates, benzyl bromide and an acid chloride. With regard to the halides, the iodides were highly reactive, bromides or chlorides gave significantly reduced yields or failed, allylic acetates failed, too. The cross-coupling partners contained a number of different functional groups, while free carboxylic acids did not deliver cross-coupling products and o,o-disubstituted arenes failed as well, a broad range of other functional groups like nitro groups, nitrile groups, ester groups, α,β-unsaturated ester groups and lactones, aldehydes, alkoxy groups, pyridyl groups, thienyl groups, unprotected phenols and anilines, even aryl azides were tolerated. The structures of one alkenylgold(I) species and of four of the cross-coupling products were proved by crystal structure analyses.

Ferric chloride hexahydrate-catalyzed highly regio- And stereoselective conjugate addition reaction of 2,3-allenoates with grignard reagents: An efficient synthesis of β,γ-alkenoates

Ferric chloride hexahydrate was shown to be an efficient catalyst for the conjugate addition of 2,3-allenoates with alkyl-, aryl-, or vinyl-Grignard reagents to synthesize polysubstituted β,γ-unsaturated alkenoates with high regio- and stereoselectivity.

Catalyzed catalysis using carbophilic Lewis acidic gold and Lewis basic palladium: Synthesis of substituted butenolides and isocoumarins

(Figure Presented) A new strategy for gold and palladium dual-catalytic reactivity and turnover, called catalyzed catalysis, enhanced the synthetic usefulness of vinylgold intermediates by providing dual-catalytic carbon-carbon cross-coupling as an alternative to protodemetalation. This protocol enabled the synthesis of substituted butenolides and isocoumarins from allyl esters. Kinetic and spectroscopic experiments support a mechanism in which the Lewis acidic gold complex catalyzes both an initial rearrangement step and a subsequent Lewis basic palladium oxidative-addition step.

Highly regioselective fluorination and iodination of alkynyl enolates

(Chemical Equation Presented) A simple yet efficient approach to various functionalized quaternary α-alkynyl α-fluoro esters and γ-iodoallenoates from readily available allenoates through an alkynyl enolate intermediate generated by LDA is presented. Reac

Synthesis of functionalized α,α-disubstituted β/alkynyl esters from allenoates through an alkynylenolate intermediate

(Chemical Equation Presented) Highly substituted α,α- disubstituted β-alkynyl esters are readily prepared from allenyl esters and either alkyl halide, acid chloride, or alkyl chloroformate, mediated by an amide base. This highly efficient and mild process

Mild and efficient palladium(II)-catalyzed racemization of allenes

Allenes undergo racemization in the presence of catalytic amounts of Pd(OAc)2/LiBr under mild conditions; the reaction proceeds via a bromopalladation-debromopalladation sequence and tolerates various functional groups.