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Synthesis 2012; 44(11): 1679-1685
DOI: 10.1055/s-0031-1290971
DOI: 10.1055/s-0031-1290971
paper
Formal [4+1] Annulation of Cyclopropyl Amides and Water Mediated by Lewis Acid: A Novel Entry to γ-Butyrolactones
Further Information
Publication History
Received 10 February 2012
Accepted after revision: 28 March 2012
Publication Date:
08 May 2012 (online)
Abstract
An efficient one-pot synthesis of substituted γ-butyrolactones from cyclopropyl amides mediated by the Lewis acid SnCl4·5H2O is reported. A mechanism involving a tandem ring-opening reaction and intramolecular cyclization reaction is proposed.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
Primary Data
- for this article are available online at http://www.thieme-connect.com/ejournals/toc/synthesis and can be cited using the following DOI:
- Primary Data
-
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For reviews on cyclopropanes, see:
For selected examples of ring-opening or ring-enlargement reactions of cyclopropanes, see:
For our recent work, see:
For reviews on donor-acceptor-substituted cyclopropanes and their reactivity, see:
For Lewis acid chelation, see:
For ring-opening of cyclopropanes, see: