55506-28-0Relevant academic research and scientific papers
NHC-Ni(0) Catalyzed Diastereodivergent Hydroacylative Enyne Cyclization: Synthesis of Heterocycles bearing γ-Enone
Yong, Xuefeng,Ng, Elvis Wang Hei,Zhen, Zibo,Lin, Xiulian,Gao, Weiwei,Ho, Chun-Yu
supporting information, p. 4164 - 4172 (2020/08/26)
NHC-Nickel(0) catalyzed 1,3- and 1,4-diastereodivergent hydroacylative heteroenyne cyclization with aldehydes was achieved (Syn-:Anti-, switchable from up to 1:99 to 98:2). Both sets of heterocyclic diastereomers are accessible via this route, with a high
Gold-catalyzed rearrangement of allylic oxonium ylides: Efficient synthesis of highly functionalized dihydrofuran-3-ones
Fu, Junkai,Shang, Hai,Wang, Zhaofeng,Chang, Le,Shao, Wenbing,Yang, Zhen,Tang, Yefeng
, p. 4198 - 4202 (2013/05/08)
"Diazo" not needed: The title reaction results in the rearrangement of oxonium ylides, which were prepared from readily available homopropargylic allylic ethers instead of diazo compounds, through two different mechanisms: a concerted 2,3-sigmatropic rearrangement, or a stepwise 1,4-allyl migration followed by a Claisen rearrangement (see scheme). Copyright
Hydroalkylation of alkynyl Ethers via a gold(I)-catalyzed 1,5-hydride shift/cyclization sequence
Jurberg, Igor Dias,Odabachian, Yann,Gagosz, Fabien
supporting information; experimental part, p. 3543 - 3552 (2010/05/01)
A series of alkynyl ethers react with an electrophilic gold(I) catalyst to produce a range of structurally complex spiro or fused dihydrofurans and dihydropyrans via a 1,5-hydride shift/cyclization sequence. This hydroalkylation process, which is performed under practical experimental conditions, can be applied to terminal as well as ester-substituted alkynes. It allows the efficient conversion of secondary or tertiary sp3 C-H bonds into new C-C bonds by the nucleophilic addition of a vinylgold species onto an oxonium intermediate. The stereoselectivity of the cycloisomerization process toward the formation of a new five- or six-membered cycle appears to be dependent on steric factors and the alkyne substitution pattern.
Conformational effects on lipase-mediated acylations of 2-substituted cyclohexanols
Tanikaga, Rikuhei,Matsumoto, Yoshimasa,Sakaguchi, Maki,Koyama, Yohei,Ono, Kentaro
, p. 6781 - 6783 (2007/10/03)
Lipase-mediated acetylations of trans- and cis-2-substituted cyclohexanols gave the corresponding (1R)-cyclohexyl acetates and (1S)-cyclohexanols in high yields and ee, but c-4-tert-butyl-c-2-ethenyl-r-1-cyclohexanol was unreactive owing to the steric interaction between the axial OH group and the axial H atoms at the 3- and 5-positions. In the cis-isomer the OH group occupies an equatorial position to bind to the lipase, and less bulky axial alkenyl and alkynyl groups might not so much prevent acetylations than an alkyl group.
Oxa-enediynes: Probing the electronic and stereoelectronic contributions to the bergman cycloaromatization
Jones, Graham B.,Wright, Justin M.,Hynd, George,Wyatt, Justin K.,Warner, Philip M.,Huber, Robert S.,Li, Aiwen,Kilgore, Michael W.,Sticca, Robert P.,Pollenz, Richard S.
, p. 5727 - 5732 (2007/10/03)
Efficient routes to three classes of 10-membered oxa-enediynes are presented. The electronic and stereoelectronic contributions to half-lives are supported by density functional theory calculations. One member of this class cyclizes to give an isochroman which binds to and degrades the aryl hydrocarbon receptor (AhR).
Synthesis of functionalized cyclopentanes, cyclohexanes and cycloheptanes by a silicon-induced domino reaction
Michel, Tycho,Kirschning, Andreas,Beier, Christian,Braeuer, Nico,Schaumann, Ernst,Adiwidjaja, Gunadi
, p. 1811 - 1821 (2007/10/03)
1,3-Functionalized cyclopentanes, -hexanes and -heptanes are obtained by addition of lithiated silyldithioacetals 7 to epoxyhomoallyl tosylates 4-6. The reaction involves a cascade of epoxide ring opening, of Brook 1,4-rearrangement and tosylate substitut
Vinyl Cations, 37. Rearrangement of Cyclic Homopropargyl Sulfonates to Condensed Cyclobutanones and Cyclopropyl Ketones
Hanack, Michael,Schuhmacher, Werner,Kunzmann, Erich
, p. 1467 - 1487 (2007/10/02)
Cyclic homopropargyl sulfonates 8 (tosylates, triflates, nonaflates, and damsylates) are prepared and solvolysed.The resulting rearrangement reactions are studied with respect to the properties of the solvents used, leaving groups, the substituent on the triple bond, and with respect to the ring size of the sulfonates 8.
