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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)


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
Issue number25
Publication statusPublished - 2004 Dec 10
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


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