Concise [4+3] cycloaddition reaction of pyrroles leading to tropinone derivatives

TETRAHEDRON LETTERS

卷:53

Article

Fuchigami, Ryuichi²  Namba, Kosuke¹  Tanino, Keiji¹ 

[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

[2] Hokkaido Univ, Grad Sch Chem Sci & Engn, Sapporo, Hokkaido 0600810, Japan

关键词: Tropinone;    [4+3] Cycloaddition reaction;    Pyrroles;    Oxyallyl cation;    Sulfur-stabilized cation;   

DOI  :  10.1016/j.tetlet.2012.07.130

来源: Elsevier

【 摘 要 】

A concise [4+3] cycloaddition reaction of pyrroles with 2-(silyloxy)allyl cations has been developed. The oxyallyl cations stabilized with a methylthio group or geminal methyl groups were generated from the corresponding allylic alcohols under the influence of a Bronsted acid (Tf2NH), respectively. The use of N-nosyl-protected pyrroles as the four-carbon unit was found to give tropinone derivatives in high yield. (C) 2012 Elsevier Ltd. All rights reserved.

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