Synlett 2013; 24(6): 661-665
DOI: 10.1055/s-0032-1318098
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© Georg Thieme Verlag Stuttgart · New York

Chiral Phosphoric Acid Catalyzed Stereoselective Spiroketalizations

Pavel Nagorny*
Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109, USA   Fax: +1(734)6474865   Email: nagorny@umich.edu
,
Zhankui Sun
Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109, USA   Fax: +1(734)6474865   Email: nagorny@umich.edu
,
Grace A. Winschel
Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109, USA   Fax: +1(734)6474865   Email: nagorny@umich.edu
› Author Affiliations
Further Information

Publication History

Received: 30 November 2012

Accepted after revision: 19 December 2012

Publication Date:
16 January 2013 (online)

Abstract

The spiroketal functionality is an important structural motif present in numerous natural products. The synthesis of chiral spiroketals is typically achieved under equilibrating conditions and only few asymmetric approaches are known. We have demonstrated that chiral phosphoric acids (CPAs) could serve as effective catalysts for enantioselective spiroketalizations as well as control the course of the corresponding diastereoselective reactions.

 
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