Rh-catalyzed intramolecular cyclization of 1-sulfonyl-1,2,3-triazole and sulfinate. Concise preparation of sulfonylated unsaturated piperidines

TETRAHEDRON LETTERS

卷:60

Article

Furukawa, Ayana¹  Hata, Takeshi^1,2  Shigeta, Masayuki¹  Urabe, Hirokazu¹ 

[1] Tokyo Inst Technol, Sch Life Sci & Technol, Midori Ku, 4259-B-59 Nagatsuta Cho, Yokohama, Kanagawa 2268501, Japan

[2] JST, PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama 3320012, Japan

关键词: Rhodium;    Triazole;    Cyclization;    Sulfinate;    Piperidine;   

DOI  :  10.1016/j.tetlet.2019.01.012

来源: Elsevier

【 摘 要 】

When 4-[3-(methanesulfinyloxy)propyl]-1-(arenesulfonyl)-1,2,3-triazoles were treated with rhodium catalysts of the type Rh-2(RCO2)(4), a new intramolecular cyclization took place to afford 2,3-didehydro-1-(arenesulfonyl)-3-(methanesulfonyl)piperidines in good yields. This reaction most likely proceeds via a new reorganization of bonds in the same molecule, consisting of the addition of the sulfur atom of sulfinate ester to the alpha-(sulfonylimino)carbene moiety generated from the sulfonyltriazole, followed by the counter attack of the sulfonylimino nitrogen to the carbon bearing the oxygen terminus of sulfinate ester. (C) 2019 Elsevier Ltd. All rights reserved.

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