Chiral Phosphoric Acid Catalyzed Stereoselective Spiroketalizations

Pavel Nagorny; Zhankui Sun; Grace A. Winschel

doi:10.1055/s-0032-1318098

Synlett, Table of Contents

Synlett 2013; 24(6): 661-665
DOI: 10.1055/s-0032-1318098

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Chiral Phosphoric Acid Catalyzed Stereoselective Spiroketalizations

Authors

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

Abstract

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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.

Key words

acetals - spiro compounds - asymmetric catalysis - oxocarbenium ion - enantioselectivity - diastereoselectivity - chiral phosphoric acids

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References

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