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Paper | Special issue | Vol 56, No. 1-2, 2002, pp.283-290
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)37
Studies on the Asymmetric Diels-Alder Reaction of Dihydropyridin-2-one with Silyloxydienes

Masamichi Yamanaka, Toshiaki Nagata, Yoshino Nakajima, Atsushi Nishida, and Masako Nakagawa*

*Graduate School of Pharmaceutical Science, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

The asymmetric Diels-Alder reaction of dihydropyridin-2-one with 2-triethylsilyloxy-1,3-pentadiene was studied in the presence of chiral aluminum reagents. Menthyloxyaluminum dichloride was the most effective catalyst and gave a hexahydroisoquinolin-2-one derivative in 44% ee as an endo-product after desilylation.