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Communication | Special issue | Vol 40, No. 2, 1995, pp.507-510
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S53
Face Selectivity in Diels-Alder Reaction of 4-Substituted Semicyclic Dienes with Dienophiles

Shigeru Nagashima, Yumiko Takaoka, Kumiko Kawakami, Motoo Shiro, and Ken Kanematsu

*Institute of Synthetic Organic Chemistry, Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan


Face selectivity in Diels-Alder reactions of the semicyclic dienes (1a) and (1b) with maleic anhydride (MA) and N-phenylmaleimide (NPM) was examined. Cycloaddition reaction of 1 with MA occurred preferentially from the diene face anti to the allylic hydroxy group, on the other hand, the cycloaddition with NPM occurred preferentially from the syn to the hydroxy group.