Title of article
A novel method for synthesizing 3-arylpyrrolidine and 4-arylpiperidine derivatives through an acid-promoted skeletal rearrangement
Author/Authors
Yokosaka، نويسنده , , Takuya and Nemoto، نويسنده , , Tetsuhiro and Hamada، نويسنده , , Yasumasa، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2013
Pages
4
From page
1562
To page
1565
Abstract
A novel method for synthesizing 3-arylpyrrolidine and 4-arylpiperidine derivatives through an acid-promoted skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel–Crafts-type addition of phenols to allyl cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and an intramolecular aza-Prins reaction, proceeded sequentially to afford 3-arylpyrrolidine and 4-arylpiperidine derivatives in good yield with high diastereoselectivity.
Keywords
pyrrolidine , Piperidine , aza-Prins reaction , skeletal rearrangement , ipso-Friedel–Crafts reaction
Journal title
Tetrahedron Letters
Serial Year
2013
Journal title
Tetrahedron Letters
Record number
1884013
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