aDepartment of Chemistry, University of the Pacific, Stockton, California, USA bDepartment of Chemistry, University of North Dakota, Grand Forks, North Dakota, USA
Аннотация:
The title reaction was observed along with cyclization in the SnCl4-promoted reaction of 2-[3,4,6-tri-O-benzyl-2-deoxy-2-(p-tolylsulfanyl)-β-D-glucopyranosyl]ethanal with pent-4-en-2-ol and this result was interpreted in terms of anchimeric assistance by sulfur to the unusual fragmentation of an intermediate alkoxycarbenium ion.
Тип публикации:
Статья
Язык публикации: английский
Образец цитирования:
V. V. Samoshin, I. P. Smoliakova, M. Han, P. H. Gross, “An unexpected allyl-transfer reaction under conditions of Lewis acid-promoted cyclization of homoallylic alcohols with aldehydes”, Mendeleev Commun., 9:6 (1999), 219–221
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc4606
https://www.mathnet.ru/rus/mendc/v9/i6/p219
Эта публикация цитируется в следующих 6 статьяx:
Hiroki Miura, Kenji Wada, Saburo Hosokawa, Masahiro Sai, Teruyuki Kondo, Masashi Inoue, “A heterogeneous Ru/CeO2 catalyst effective for transfer-allylation from homoallyl alcohols to aldehydes”, Chem. Commun., 2009, no. 27, 4112
Sayuri Hayashi, Koji Hirano, Hideki Yorimitsu, Koichiro Oshima, “Gallium-mediated allyl transfer from bulky homoallyl alcohol to aldehydes or alkynes: Control of dynamic σ-allylgalliums based on retro-allylation reaction”, Journal of Organometallic Chemistry, 692:1-3 (2007), 505
Teck-Peng Loh, Qi-Ying Hu, Li-Ting Ma, “Stereocontrolled Synthesis of Linear 22R-Homoallylic Sterols via a Triflic Acid-Catalyzed 2-Oxonia Cope Rearrangement”, Org. Lett., 4:14 (2002), 2389
Satwinder Singh, Subodh Kumar, Swapandeep Singh Chimni, “Chemoenzymatic synthesis of optically active heterocyclic homoallylic and homopropargylic alcohols”, Tetrahedron: Asymmetry, 13:24 (2002), 2679
Teck-Peng Loh, Kui-Thong Tan, Qi-Ying Hu, “A new mechanistic proposal for the origin of α-homoallylic alcohols in indium-mediated allylation reactions in water”, Tetrahedron Letters, 42:49 (2001), 8705
Vyacheslav V. Samoshin, Irina P. Smoliakova, Mingming Han, Paul H. Gross, “ChemInform Abstract: An Unexpected Allyl‐Transfer Reaction under Conditions of Lewis Acid‐Promoted Cyclization of Homoallylic Alcohols with Aldehydes.”, ChemInform, 31:20 (2000)
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