54526-80-6

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 6956, 1993 DOI: 10.1021/jo00077a008

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 17356-19-3 1-ethynylcyclopentanol 
• 107644-67-7 methyl (Z)-3-(1-cyclopenten-1-yl)-2-propenoate 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 292638-85-8 acrylic acid methyl ester 
• 287944-10-9 2-cyclopent-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 
• 36839-94-8 cyclopent-1-en-1-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 124-41-4 sodium methylate 
• 693-89-0 1-methylcyclopent-1-ene 
• 14090-83-6 methyl 2-phenylsulfinylacetate 

Relevant academic research and scientific papers

Synthesis of Dienoic Acids and Esters by Cationic Palladium Complex Catalyzed Carbonylation of Alkynols and Alkynediols

The cationic palladium(II) aquo hydride, trans-(Cy3P)2Pd(H)(H2O)(+)BF4(-), is an excellent catalyst for the carbonylation of alkynols to dienoic acids and esters and of alkynediols to cross-conjugated diesters.

Ruthenium-Catalyzed Oxidative Cross-Coupling Reaction of Activated Olefins with Vinyl Boronates for the Synthesis of (E, E)-1,3-Dienes

An oxidative cross-coupling reaction between activated olefins and vinyl boronate derivatives has been developed for the highly stereoselective construction of synthetically useful (E,E)-1,3-dienes. The highlight of this reaction is that exclusive stereoselectivity (only E,E-isomer) was achieved from a base-free, ligand-free, and mild catalytic condition with a less expensive [RuCl2(p-cymene)]2 catalyst.

An expedient variant of heck reaction of alkenyl nonaflates: Homogeneous ligand-free palladium catalysis at room temperature

A mechanistic study on the ligand-free room-temperature Heck reaction of alkenyl nonafluorobutanesulfonates (nonaflates) is described. Kinetic data obtained from poisoning experiments, centrifugation and variation of catalyst loading consistently provide

One-pot transformation of silyl enol ethers into 1,3-dienes: In situ generation of alkenyl nonaflates and subsequent Heck reactions - Scope and limitations

Palladium-catalysed reactions between methyl acrylate and the isolated alkenyl nonaflates 2a, 2d and 2e proceed without difficulties, furnishing the desired 1,3-dienes 3, 14 and 15 in good yields. The use of other alkenyl nonaflates and olefins in this Heck reaction was also examined. The main purpose of this study was the development of an in situ generation of the required alkenyl nonaflates 2 from the corresponding silyl enol ethers 1 and their one-pot transformation into 1,3-dienes. Thus, the previously described fluoride-promoted exchange of the trimethylsilyl substituent of typical enol ethers 1 for a nonafluorobutylsulfonyl group was directly combined with the palladium-catalysed coupling step. This sequence allowed the efficient transformation of a variety of silyl enol ethers 1 into highly substituted 1,3-dienes in a practical one-pot procedure. The scope and limitations, together with the chemo- and stereoselectivity, of this process are discussed. A particular intriguing example involves a one-pot synthesis of silyl enol ether 1j by means of a Diels-Alder reaction, subsequent nonaflation and a Heck reaction with tert-butyl acrylate, furnishing the highly functionalised 1,3-diene 30 in good overall yield. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

On the Regioselectivity and Stereoselectivity of the Carbene Transfer from Fischer Carbene Complexes to Trisubstituted Electron-Deficient 1,3-Dienes

Thermal reactions of Fischer carbene complex 1 with trisubstituted electron-deficient 1,3-dienes 7, 8, 23, 25, 32, and 35 provided highly substituted vinylcyclopropanes in good yields.The carbene transfer proceeds highly regioselectively favouring cyclopropanation of the double bond not bearing the ester function.In addition, the diastereoselectivity is generally fairly high in preference of cyclopropanes with the methoxy group cis-positioned with respect to the olefin moiety.The reaction of methylcarbene complex 2 with diene ester 8 displays inversed regioselectivity.These ovservations are discussed together with solvent effects, and a mechanistic rationale is presented. - Key Words: Chromium complexes/ Carbene complexes/ 1,3-Dienes, electron-deficient/ Cycloadditions/ Vinylcyclopropanes, donor-acceptor-substituted/ Diastereoselectivity/ Regioselectivity

A FACILE, STEREOSELECTIVE PREPARATION OF (Z)-2,4-PENTADIENOATES BY FAVORSKII REARRANGEMENT

Reaction of 1,3,4-tribromo-2-alkanones, efficiently prepared by direct bromination of the parent enone, with methanolic sodium methoxide gives methyl (Z)-2,4-pentadienoates with high (Z) selectivity about the α,β-double bond.