Journal of the Chemical Society. Perkin transactions I p. 2639 - 2646 (1988)
Update date:2022-08-05
Topics:
Padwa, Albert
Carter, Stephen P.
Chiacchio, Ugo
Kline, Donald N.
Perumattam, John
1,3-Dipolar cycloaddition of nitrones to phenylsulphonylallene gives in high yield and with complete regiospecificity 5-methyleneisoxazolidines.These on treatment with base and subsequent reaction with electrophiles afford both α- and γ-substituted products.With methyl iodide as the electrophile, only the α-methylated product was isolated.In contrast, reaction of the 5-exo-methylene-4-phenylsulphonylisoxazolidine with allyl bromide afforded the γ-allyated product.Formation of this was shown to be via direct γ-attack, rather than by α-attack, followed by a 3,3-sigmatropic rearrangement.Further studies show that the product ratio is controlled by a sensitive interplay between thermodynamic and steric factors and is very dependent on the nature of the electrophile used.
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