Regio- and diastereoselective cycloaddition of N-methyl nitrones derived from 3-(allylamino)propionaldehydes

Authors
Tanaka, M Hikata, J Yamamoto, H Noguchi, M
Citation
M. Tanaka et al., Regio- and diastereoselective cycloaddition of N-methyl nitrones derived from 3-(allylamino)propionaldehydes, HETEROCYCLE, 55(2), 2001, pp. 223-226
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
55
Issue
2
Year of publication
2001
Pages
223 - 226
Database
ISI
SICI code
0385-5414(20010201)55:2<223:RADCON>2.0.ZU;2-K
Abstract
Regio- and stereochemistry of intramolecular cycloaddition of N-methyl nitr ones derived from 3-(allylamino)propionaldehydes was discussed; the methyl substituent at the 3-position in the nitrones (11) provided a highly contro lled course of the cycloaddition to give predominantly syn-cis-fused adduct s (12), while the reaction of the corresponding 2-methyl nitrone (7a) gave syn-cis- and anti-cis-fused (8a) and syn- and anti-bridged adducts (9a).