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Synfacts 2011(10): 1093-1093  
DOI: 10.1055/s-0030-1261133
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Cu(II)-Catalyzed Synthesis of Substituted Tetrahydropyrans

Contributor(s): Mark Lautens, Patrick T. Franke
A. K. Ghosh*, D. R. Nicponski
Purdue University, West Lafayette, USA
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Publication History

Publication Date:
20 September 2011 (online)

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Significance

The authors have developed a mild Cu(OTf)2-bisphosphine-catalyzed reaction for the synthesis of substituted tetrahydropyran derivatives. The reaction proceeds via an olefin migration followed by a Prins cyclization to provide a range of tetrahydropyran derivatives in good yields and excellent trans diastereoselectivity.