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Communication | Special issue | Vol 52, No. 3, 2000, pp.1041-1045
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S126
Optically Active Aldiminato Cobalt(II) Complex Catalyst for Enantioselective Hetero Diels-Alder Reaction

Tohru Yamada,* Satoko Kezuka, Tsuyoshi Mita, and Taketo Ikeno

*Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan

Abstract

Among various aldiminato metal complexes, the optically active cobalt(II) complex efficiently catalyzed the enantioselective hetero Diels-Alder reaction of aromatic aldehydes with 1-methoxy-[3-(tert-butyldimethylsilyl)oxy]- 1,3-butadiene. In the presence of 0.5 mol% of the catalyst, the reaction smoothly proceeded and ortho substituents of the dienophiles that could chelate to the catalyst significantly accelerated the reaction to improve the chemical and optical yields.