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Communication | Regular issue | Vol 55, No. 2, 2001, pp.223-226
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9054
Regio- and Diastereoselective Cycloaddition of N-Methyl Nitrones Derived from 3-(Allylamino)propionaldehydes

Masayuki Tanaka, Jun Hikata, Hidetoshi Yamamoto, and Michihiko Noguchi*

*Department of Applied Chemistry, Faculty of Engineering, Yamaguchi University, 2-16-1 Tokiwadai, Ube, Yamaguchi 755-8611, Japan


Regio- and stereochemistry of intramolecular cycloaddition of N-methyl nitrones derived from 3-(allylamino)propionaldehydes was discussed; the methyl substituent at the 3-position in the nitrones (11) provided a highly controlled course of the cycloaddition to give predominantly syn-cis-fused adducts (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).