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Short Paper | Special issue | Vol 99, No. 2, 2019, pp.1330-1341
Published online, 16th November, 2018
DOI: 10.3987/COM-18-S(F)54
Bimetallic Lewis Acid Template-Mediated Enantioselective Hetero-Diels-Alder Reactions of 4-Siloxy-2,4-pentadienols

Jun Ishihara,* Yuka Ohzono, Kengo Oka, Yasuhiro Urayama, and Susumi Hatakeyama

*Graduate School of Biomedical Sciences, Nagasaki University, Nagasaki, 852-8521, Japan

Abstract

Enantioselective hetero-Diels-Alder reactions catalyzed by a bimetallic Lewis acid template are described. The hetero-Diels-Alder reactions of 4-siloxy-2,4-pentadienols and various dienophiles by the chiral H8-BINOL template provide a general entry into the substituted dihydropyrans with good enantioselectivities. This protocol is also applicable to a dihydropirazine formation.