Synthesis of trans -Cycloalkenes via Enantioselective Cyclopropanation and Skeletal Rearrangement

Tomoya Miura, Takayuki Nakamuro, Chia Jung Liang, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

67 Citations (Scopus)

Abstract

An efficient one-pot two-step procedure for asymmetric synthesis of piperidine-fused trans-cycloalkenes is reported. The method comprises the initial enantioselective installation of another cyclopropane ring onto methylenecyclopropanes and the subsequent thermal skeletal rearrangement in which the installed and inherent cyclopropane rings are both opened. A concerted mechanism is proposed for the latter thermal rearrangement reaction together with a closed transition state model.

Original languageEnglish
Pages (from-to)15905-15908
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number45
DOIs
Publication statusPublished - Nov 12 2014
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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