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

Journal Article (Journal Article)

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. © 1991.

Full Text

Duke Authors

Cited Authors

  • Baldwin, SW; McFadyen, RB; Aubé, J; Wilson, JD

Published Date

  • January 1, 1991

Published In

Volume / Issue

  • 32 / 35

Start / End Page

  • 4431 - 4434

International Standard Serial Number (ISSN)

  • 0040-4039

Digital Object Identifier (DOI)

  • 10.1016/0040-4039(91)80004-P

Citation Source

  • Scopus