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Communication | Special issue | Vol 42, No. 1, 1996, pp.129-133
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S43
High Pressure Mediated Asymmetric Diels-Alder Reaction of Chiral Sulfinylacrylate Derivatives with Furan and 2-Methoxyfuran

Yoko Nakajima Yamakoshi, Wei-Ying Ge, Jun Sugita, Kazuya Okayama, Tamiko Takahashi, and Toru Koizumi

*Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, 2630 Sugitani, Toyama, Toyama 930-0194, Japan


Asymmetric Diels-Alder reaction of chid sulfinylacrylate derivatives (1 and 2) with furan (3) and 2-methoxyfuran (4) proceeded under high pressure (1.2 GPa) conditions to give endo cycloadducts (6c-f). The absolute configuration of adduct (6) was confirmed by conversion of 6e to (-)-COTC (9).