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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

The Prins Reaction: Advances and Applications

Author(s): Isidro M. Pastor and Miguel Yus

Volume 11, Issue 10, 2007

Page: [925 - 957] Pages: 33

DOI: 10.2174/138527207781024067

Price: $65

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

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