A comparison between zeolites and crystalline state as reaction media: Asymmetric induction during photocyclization of α-mesitylacetophenones to 2-indanols

Arunkumar Natarajan, V. Ramamurthy, Joel T. Mague

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

The effectiveness of chiral auxiliaries in inducing diastereoselectivity during photocyclization of ten differnt α-mesitylacetophenones to 2-indanols in crystalline state and as zeolite inclusion complexes has been examined. In the systems examined the chiral auxiliary functioned better within zeolites than in crystals. Crystal structure analysis of three α-mesitylacetophenones revealed that the low chiral induction in the crystalline state is either due to the presence of conformational isomerism in the reactant part of the molecule or the absence of communication between the chiral auxiliary and the reactant part of the ketone.

Original languageEnglish (US)
Pages (from-to)71-84
Number of pages14
JournalMolecular crystals and liquid crystals
Volume456
Issue number1
DOIs
StatePublished - Oct 1 2006

Keywords

  • δ-hydrogen abstraction
  • Chiral induction
  • Crystalline state
  • Diastereoselectivity
  • Mesitylacetophenones
  • Photocyclization
  • Zeolites

ASJC Scopus subject areas

  • Condensed Matter Physics

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