Asymmetric Synthesis of Protected Cyclohexenylamines and Cyclohexenols by Rhodium-Catalyzed [2+2+2] Cycloaddition

Koji Masutomi, Haruki Sugiyama, Hidehiro Uekusa, Yu Shibata, Ken Tanaka

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

It has been established that cationic rhodium(I)/axially chiral biaryl bis(phosphine) complexes catalyze the asymmetric [2+2+2] cycloaddition of 1,6-enynes with electron-rich functionalized alkenes, enamides, and vinyl carboxylates, to produce the corresponding protected cyclohexenylamines and cyclohexenols. Interestingly, regioselectivity depends on structures of substrates. The present cycloaddition was successfully applied to the enantioselective total synthesis of (−)-porosadienone by using the amide moiety as a leaving group.

Original languageEnglish
Pages (from-to)15373-15376
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number49
DOIs
Publication statusPublished - 2016 Jan 1
Externally publishedYes

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Keywords

  • asymmetric catalysis
  • cycloadditions
  • enamides
  • reaction mechanisms
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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