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Communication | Special issue | Vol 50, No. 1, 1999, pp.53-56
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)26
Asymmetric Diels-Alder Reaction of Optically Active 3-(3,3,3-Trifluoropropenylsulfonyl)oxazolidine: Synthesis of (8R)-8-Trifluoromethyl-2-oxa-6-thia-5-azatricyclo[,5]undecane-6,6-dioxide

Takashi Okano,* Tomoyuki Nagai, Shoji Eguchi, and Hiroshi Kimoto

*Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya, Aichi 464-8601, Japan


Asymmetric Diels-Alder reaction of optically active 3-(3,3,3-trifluoro-propenylsulfonyl)-1,3-oxazolidine (1) with several dienes gave adducts regio- and stereoselectively in 69-78% de. Acetalization of 2-methoxybutadiene adduct with catechol gave tricyclic sultam-oxazolidine (15), wich could be readily deprotonated and gave bridgehead sulfide (16).