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Cationic gold(I)-mediated intramolecular cyclization of 3-alkyne-1,2-diols and 1-amino-3-alkyn-2-ols: a practical route to furans and pyrroles.

Authors
  • Egi, Masahiro
  • Azechi, Kenji
  • Akai, Shuji
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Nov 05, 2009
Volume
11
Issue
21
Pages
5002–5005
Identifiers
DOI: 10.1021/ol901942t
PMID: 19780532
Source
Medline
License
Unknown

Abstract

The intramolecular cyclizations of the 3-alkyne-1,2-diols and the 1-amino-3-alkyn-2-ols with a low catalyst loading (0.05-0.5 mol %) of (Ph(3)P)AuCl-AgNTf(2) or (Ph(3)P)AuCl-AgOTf proceeded at room temperature to provide a variety of substituted furans and pyrroles in excellent yields (85-98% yields). This method is also fully applicable to the conversion of several dozen grams of the substrate using only 0.05 mol % each of the Au and Ag catalysts.

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