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Synfacts 2007(4): 0407-0407
DOI: 10.1055/s-2007-968360
DOI: 10.1055/s-2007-968360
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Intermolecular Acetal-Initiated Cationic Polyene Cyclizations
Y.-J. Zhao, S.-S. Chng, T.-P. Loh*
Nanyang Technological University, Singapore
Further Information
Publication History
Publication Date:
23 March 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200704/lookinside/thumbnails/10.1055-s-2007-968360-1.jpg)
Significance
This report describes the intermolecular acetal-initiated polyene cyclization induced by SnCl4. The authors do a nice job in optimizing the reaction and find a chiral templated acetal that allows for considerably high dr values. The absolute and relative stereochemistry were determined for the products through derivatization and X-ray crystallography. Some of the cyclization products were also functionalized to various terpenes. Importantly, this report does not require the sometimes difficult and tedious incorporation of the acetal into the cyclization precursor.