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 language | English (US) |
|---|---|
| Pages (from-to) | 71-84 |
| Number of pages | 14 |
| Journal | Molecular crystals and liquid crystals |
| Volume | 456 |
| Issue number | 1 |
| DOIs | |
| State | Published - 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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Natarajan, A., Ramamurthy, V., & Mague, J. T. (2006). A comparison between zeolites and crystalline state as reaction media: Asymmetric induction during photocyclization of α-mesitylacetophenones to 2-indanols. Molecular crystals and liquid crystals, 456(1), 71-84. https://doi.org/10.1080/15421400600786355