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1. Diastereoselectivity in the intramolecular cycloaddition reactions of nitrones derived from 5-alkenals and chiral hydroxylamines

Author

Jeffrey Aubé, J. D. Wilson, Steven W. Baldwin, and R.B. McFadyen

Subjects
chemistry.chemical_classification, Intramolecular reaction, Bicyclic molecule, Stereochemistry, Organic Chemistry, Diastereomer, Biochemistry, Aldehyde, Cycloaddition, Nitrone, chemistry.chemical_compound, Hydroxylamine, chemistry, Intramolecular force, Drug Discovery
Abstract

Intramolecular cycloaddition of the nitrones derived from a series of 5-alkenals and α-methylbenzyl hydroxylamine leads to mixtures of diastereomeric products in the range of 1.7/1 to 16/1. Cyclization of a series of fifteen 5-alkenyl nitrones with a chiral group on nitrogen afforded diastereomeric isoxazolidines in ratios ranging from 1.7/1 to 16/1. When R* = (S)-α-methylbenzyl, C6a of the major product was also S in those cases known.

Published
1991
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