N-Alkenyl nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 6. Allylic stereocontrol in the intramolecular cyclisation of monosubstituted nitrones
- 1 January 1994
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 16,p. 2205-2215
- https://doi.org/10.1039/p19940002205
Abstract
The Intramolecular, thermal dipolar cycloadditions of the (Z)-N-alk-4-enyl nitrones 18–21, 34 and 35 bearing a single, allylic substituent were investigated. Certain alkoxy substituted nitrones 18–21 showed a remarkable preference for the formation of axially substituted isoxazolidines 22a-24a, whereas the, propyl and trifluoromethyl substituted nitrones 35 and 34 gave the equatorially substituted cycloadducts 37 and 36a respectively, consistent with the involvement of ‘chair-like’ transition states 38.Keywords
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