13633-29-9Relevant academic research and scientific papers
Copper-Catalyzed Propargylic Reduction with Diisobutylaluminum Hydride
Kim, Yuna,Lee, Hanseul,Park, Sunga,Lee, Yunmi
, p. 5478 - 5481 (2018/09/13)
A mild and efficient method for the synthesis of allenes through selective copper-catalyzed hydride addition to propargylic chlorides using commercially available diisobutylaluminum hydride has been developed. This transformation, which is promoted by a readily accessible N-heterocyclic carbene-copper complex, provides a wide range of new and versatile functionalized allenes in good to excellent yields with high regio- A nd stereoselectivities.
Synthesis of mono- and 1,3-disubstituted allenes from propargylic amines via palladium-catalysed hydride-transfer reaction
Nakamura, Hiroyuki,Ishikura, Makoto,Sugiishi, Tsuyuka,Kamakura, Takaya,Biellmann, Jean-Francois
experimental part, p. 1471 - 1477 (2008/10/09)
Mono- and 1,3-disubstituted allenes were synthesized from the corresponding propargylamines via palladium-catalysed hydride-transfer reaction. In the current transformation, propargylic amines can be handled as allenyl anion equivalents and introduced int
A new method for synthesis of allenes, including an optically active form, from aldehydes and alkenyl aryl sulfoxides by sulfoxide-metal exchange as the key reaction and an application to a total synthesis of male bean weevil sex attractant
Satoh, Tsuyoshi,Hanaki, Noriko,Kuramochi, Yuko,Inoue, Yujiro,Hosoya, Kayo,Sakai, Ken
, p. 2533 - 2549 (2007/10/03)
The sulfoxide-metal exchange reaction of β-acetoxy sulfoxides or β-mesyloxy sulfoxides, which were derived from alkenyl aryl sulfoxides and aldehydes in two steps, with a Grignard reagent or alkyllithium at low temperature gave allenes in good yields. Optically active allenes were synthesized starting from optically active 2-substituted ethenyl p-tolyl sulfoxides. A synthesis of (-)-methyl (E)-2,4,5-tetradecatrienoate, a male bean weevil sex attractant, was realized by this method.
A new method for synthesis of allenes, including an optically active form, from aldehydes and alkenyl aryl sulfoxides with carbon-carbon bond- formation
Satoh, Tsuyoshi,Kuramochi, Yuko,Inoue, Yujiro
, p. 8815 - 8818 (2007/10/03)
Ligand exchange reaction of β-mesyloxy sulfoxides or β-acetoxy sulfoxides, which were derived from alkenyl aryl sulfoxides and aldehydes in two steps, with n-BuLi or EtMgBr at low temperature gave allenes in good yields. Optically active allenes were synthesized starting from optically active 2-phenylethenyl p-tolyl sulfoxides.
Solvolysis of 2,2-dialkylvinyl iodonium salt: Alkyl participation and possibility of a primary vinylic cation intermediate
Okuyama, Tadashi,Yamataka, Hiroshi,Ochiai, Masahito
, p. 2761 - 2769 (2007/10/03)
Solvolysis of (E)- and (Z)-2-methyl-5-phenyl-1-pentenyl(phenyl)iodonium tetrafiuoroborate (1·BF4) was carried out in various alcohols, acetic acid, and aqueous solutions at 60 °C. Products (after acid hydrolysis) include iodobenzene and 2-methyl-5-phenylpentanal as well as rearranged ones: 6- phenyl-2-hexanone, 6-phenyl-3-hexanone, 6-phenyl-2-hexyne, 6-phenyl- 1,2- hexadiene, and 6-phenyl-2,3-hexadiene. The products of α-elimination, including 1-methyl-3-phenyl-1-cyclopentene, were also obtained in methanol and ethanol. Solvolysis of the E isomer (E)-1 is faster than that of (Z)-1 in every solvent examined. The percentage of rearrangement is higher with (E)-1 than with (Z)-1, and the main rearranged products are those of migration of the alkyl group trans to the iodonio group, but migration of the cis alkyl group is also involved. Theoretical calculations suggest that interconversion between the secondary Vinylic cations by 1,2-hydride shift is rapid. These results show that a major heterolysis reaction occurs with β-alkyl participation to directly give a secondary vinylic cation, but stereochemistry of the unrearranged substitution products suggests that formation of the primary vinylic cation is also involved in less nucleophilic solvents like acetic acid and 2,2,2-trifluoroethanol.
Solvolysis of β,β-dialkylvinyliodonium salt: Primary vinyl cation intermediate and alkyl participation
Okuyama, Tadashi,Sato, Koichi,Ochiai, Masahito
, p. 1177 - 1178 (2007/10/03)
Solvolysis of both E and Z isomers of a β,β-dialkylvinyl-(phenyl)iodonium salt gave extensively rearranged products. A mechanism involving a primary vinyl cation intermediate as well as the alkyl participation leading to secondary vinyl cations is proposed.
General method for preparation of allenic zinc reagents by three-carbon homologation of triorganozincates: Convergent three-component coupling of propargylic substrates, triorganozincates, and electrophilic reagents
Harada, Toshiro,Katsuhira, Takeshi,Osada, Atsushi,Iwazaki, Katsuhiro,Maejima, Keiji,Oku, Akira
, p. 11377 - 11390 (2007/10/03)
Allenic zinc reagents (R1R2C=C=C(R3)ZnL) are efficiently prepared by the reaction of propargylic substrates (R1R2C(X)C≡CH, X = MeSO2O,Cl, R2NCO2) with a variety of tri
