Tetrahedron

Synthesis of chiral spiro 3-oxazolin-5-one 3-oxides (chiral nitrones) via a nitrosoketene intermediate and their asymmetric 1, 3-dipolar cycloaddition reactions leading …

N Katagiri, M Okada, Y Morishita, C Kaneko

Index: Katagiri, Nobuya; Okada, Makoto; Morishita, Yoshihiro; Kaneko, Chikara Tetrahedron, 1997 , vol. 53, # 16 p. 5725 - 5746

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Citation Number: 45

Abstract

Cycloaddition of chiral cyclic ketones such as (−)-menthone,(+)-nopinone, and (+)- camphenilone to nitrosoketene generated by thermolysis of 5-hydroxyimino-2, 2-dimethyl-1, 3-dioxane-4, 6-dione gave the corresponding chiral spiro 3-oxazolin-5-one 3-oxides (chiral cyclic nitrones). These nitrones underwent asymmetric 1, 3-dipolar cycloaddition reactions with electron rich olefins to give the corresponding oxazolidine derivatives with high ...

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