Acetoxyl group directed cyclization promoted by SmI2: Directing group determined stereocomplementarity

Toshiyuki Kan, Seijiro Hosokawa, Shinji Nara, Hiroaki Tamiya, Haruhisa Shirahama, Fuyuhiko Matsuda

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Abstract

Complete reversal of diastereoselectivity was observed in the SmI 2-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI2-induced ketyl-olefin coupling cyclizations of the δ-hydroxy ketone 1 and δ-acetoxy ketone 3.

Original languageEnglish
Pages (from-to)8956-8958
Number of pages3
JournalJournal of Organic Chemistry
Volume69
Issue number25
DOIs
Publication statusPublished - 2004 Dec 10

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ASJC Scopus subject areas

  • Organic Chemistry

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