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Synfacts 2008(4): 0395-0395  
DOI: 10.1055/s-2008-1042870
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Salen-Cr(III)Cl-Catalyzed Enantioselective Iodoetherification of γ -Hydroxy-cis-alkenes

Contributor(s): Hisashi Yamamoto, Pingfan Li
H. Y. Kwon, C. M. Park, S. B. Lee, J.-H. Youn, S. H. Kang*
KAIST and Sun Moon University, Korea
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Publikationsverlauf

Publikationsdatum:
19. März 2008 (online)

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Significance

Highly enantioselective electrophile-mediated cyclization reactions are not as often seen as their diastereoselective versions. The present work shows an improvement of enantio­selectivities using less than 10 mol% chiral salen-chromium(III) catalyst for the enantioselective iodoetherification of γ-hydroxy-cis-alkenes to generate synthetically useful 2-substituted tetrahydrofurans. Application of this methodology leads to an asymmetric synthesis of swainsonine.