ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7

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Stereoselectivity in the cycloaddition of chiral glyceraldehyde derived nitrone to styrene

J. Kuban, I. Blanarikova, L. Fisera, and N. Pronayova

 

Abstract: The stereoselectivity of 1,3-dipolar cycloadditions of C-alpha-alkoxy-substituted chiral nitrones with styrene was investigated. Diastereoselectivity far the glyceraldehyde derived nitrone cycloaddition to the styrene was found w(r) 73:11:9:7. The major product was found to have the C-3/C-4' erythro and C-3/C-5cis relative stereochemistry. It likely derives via less hindered Endo attack and in an antiperiplanar manner with respect to the largest methylene group of the dioxolane ring. The cycloaddition with L-lactate derived nitrone was less selective and stereoisomers were found in the ratio of w(r) = 39:30:20:11.

 

Chemical Papers 51 (6B) 378–382 (1997)

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