Diastereodifferentiating [2+2] photocycloaddition of a chiral cyclohexenone with cyclopentene in supercritical carbon dioxide using a flow microreactor

Yasuhiro Nishiyama*, Ryota Mori, Kosei Nishida, Hiroki Tanimoto, Tsumoru Morimoto, Kiyomi Kakiuchi

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The diastereodifferentiating [2+2] photocycloaddition of a chiral cyclohexenone with cyclopentene was performed in supercritical carbon dioxide (scCO2) using a flow microreactor. In all cases examined, the microreactor gave higher conversions than the batch system because of the very short path length of the microreactor. Additionally, by using the microreactor, accurate temperature control produced higher diastereoselectivity. These distinguished findings can be attributed to the synergistic effect of superior light penetration in the microreactor and the unique solvent property (clustering effect) of scCO2.

Original languageEnglish
Pages (from-to)185-189
Number of pages5
JournalJournal of Flow Chemistry
Volume4
Issue number4
DOIs
StatePublished - 2014/12/10

Keywords

  • [2+2] photocycloaddition
  • diastereoselective reaction
  • flow microreactor
  • supercritical carbon dioxide

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Fluid Flow and Transfer Processes
  • Organic Chemistry

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