Abstract
A study of regio- and stereo-selectivity in the cycloaddition reactions of a series of symmetrical and unsymmetrical 1,2-disubstituted alkenestothechiral, internally H-bonded N-(2-hydroxy-1-phenyl)methylenenitrone, has been carried out. The regioselectivity observed in the addition reactions is explained in terms of frontier orbital interactions. The alkenes having a hydroxymethyl substituent at the allylic position are found to undergo regio- as well as highly stereo-selective cycloaddition reactions in the presence of anhydrous magnesium bromide.
| Original language | English |
|---|---|
| Pages (from-to) | 38-47 |
| Number of pages | 10 |
| Journal | Journal of Chemical Research |
| Issue number | 1 |
| DOIs | |
| State | Published - Jan 2008 |
Keywords
- Asymmetric induction
- Chiral methylenenitrone
- Diastereoselection
- Dipolar cycloddition
- Lewis acid catalyst
ASJC Scopus subject areas
- General Chemistry
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