Abstract
The acid-catalyzed alkene-aldehyde condensation, known as the Prins reaction, is reviewed. Lewis acids, organic acids and supported catalysts have been reported to assist both the Prins acyclic reaction and the Prins cyclization. Acetals and oxocarbenium ions (generated from aldehydes and alcohols) have been described as reacting systems in the Prins reaction. Prins cyclizations have been used to form mainly five- and six-membered rings, albeit formation of seven to nine rings have been described. The Prins reaction (and cyclization) has been developed as a key strategic element in the total synthesis of different natural products.
Keywords: Organic Acid, styrenes, hetero Diels-Alder reaction, Lewis acid catalysts, stereoselective Prins reaction
Current Organic Chemistry
Title: The Prins Reaction: Advances and Applications
Volume: 11 Issue: 10
Author(s): Isidro M. Pastor and Miguel Yus
Affiliation:
Keywords: Organic Acid, styrenes, hetero Diels-Alder reaction, Lewis acid catalysts, stereoselective Prins reaction
Abstract: The acid-catalyzed alkene-aldehyde condensation, known as the Prins reaction, is reviewed. Lewis acids, organic acids and supported catalysts have been reported to assist both the Prins acyclic reaction and the Prins cyclization. Acetals and oxocarbenium ions (generated from aldehydes and alcohols) have been described as reacting systems in the Prins reaction. Prins cyclizations have been used to form mainly five- and six-membered rings, albeit formation of seven to nine rings have been described. The Prins reaction (and cyclization) has been developed as a key strategic element in the total synthesis of different natural products.
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Cite this article as:
Isidro M. Pastor and Miguel Yus , The Prins Reaction: Advances and Applications, Current Organic Chemistry 2007; 11 (10) . https://dx.doi.org/10.2174/138527207781024067
DOI https://dx.doi.org/10.2174/138527207781024067 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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