226089-86-7Relevant articles and documents
Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives
Yamada, Tsuyoshi,Park, Kwihwan,Tachikawa, Takumu,Fujii, Akiko,Rudolph, Matthias,Hashmi, A. Stephen K.,Sajiki, Hironao
, p. 1883 - 1888 (2020/03/03)
An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experiments revealed that the cyclization occurs via a 1,5-H shift. The cyclic acetal group promoted the 1,5-H shift by activating the benzylic C-H bond and preventing the migration of the alkoxy group by tethering both alkoxy groups.
Integrated Chemical Process: One-Pot Double Elimination Method for Acetylenes
Orita, Akihiro,Yoshioka, Naonori,Struwe, Petra,Braier, Arnold,Beckmann, Anke,Otera, Junzo
, p. 1355 - 1363 (2007/10/03)
A novel one-pot process for synthesis of acetylenes has been achieved in which the following series of steps are integrated: addition of an α-anion of sulfone to aldehyde; trapping of the resulting adduct to incorporate a leaving group, and double elimination of this intermediate. Consolidation of Peterson elimination renders the process much simpler. This method provides a convenient and high-yielding access to a variety of enynes and polyynes as well as to functionally substituted aryl acetylenes containing halogen(s) or acetal groups, which are useful building blocks for aryl acetylene scaffolds. Iteration of the one-pot generation of acetylenic bonds provides a new metodology for the buildup of aryl acetylene skeletons.
