Use of Cyclopropane as C1 Synthetic Unit by Directed Retro-Cyclopropanation with Ethylene Release

Sobi Asako, Takaaki Kobashi, Kazuhiko Takai

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Cyclopropanation of alkenes is a well-established textbook reaction for the synthesis of cyclopropanes, where a "high-energy" carbene species is exploited to drive the reaction forward. However, little attention has been focused toward molecular transformations involving the reverse reaction, retro-cyclopropanation (RC). This is because of difficulties associated with both cleaving the two geminal C-C single bonds and exploiting the generated carbenes for further transformations in an efficient and selective manner. Here, we report that a molybdenum-based catalytic system overcomes the above challenges and effects the RC of cyclopropanes bearing a pyridyl group with the release of ethylene (alkene) and the subsequent intramolecular cyclization leading to pyrido[2,1-a]isoindoles. The reaction allows for the uncommon use of cyclopropanes as C1 synthetic units in contrast to most conventional reactions in which cyclopropanes are used as C3 synthetic units. We anticipate that this new strategy will pave the way for C1 cyclopropane chemistry.

Original languageEnglish
Pages (from-to)15425-15429
Number of pages5
JournalJournal of the American Chemical Society
Volume140
Issue number45
DOIs
Publication statusPublished - Nov 14 2018

ASJC Scopus subject areas

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

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