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■ Asymmetric Synthesis of Isoquinuclidine by Diels-Alder Reaction of 1,2-Dihydropyridine and Chiral Dienophile Utilizing a Chiral Lewis Acid

Masafumi Hirama, Chonticha Suttibut, N. D. M. Romauli Hutabarat, Chigusa Seki,* Noritaka Sakuta, Takefumi Tsuchiya, Yoshihito Kohari, Hiroto Nakano, Koji Uwai, Nobuhiro Takano, Mitsukuni Yasui, Yuko Okuyama, Kenichi Osone, Mitsuhiro Takeshita, and Haruo Matsuyama*

*Department of Applied Chemistry, Graduate School of Engineering, Muroran Institute of Technology, 27-1 Mizumoto, Muroran, Hokkaido 050-8585, Japan

Abstract

The asymmetric Diels-Alder reaction of 1-phenoxycarbonyl-1,2-dihydropyridine 1 with 3-acryloyl (4S)-4-benzyl-1,3-oxazolidin-2-one (4S)-2 {or (4R)-2} in the presence of Ti-TADDOLate 4 as a chiral Lewis acid afforded the chiral isoquinuclidine derivative endo-(4’S)-3 in high yield (99%) with high diastereoselectivity (up to 92% d.e.). The reaction exhibits a strong match-mismatch effect. The stereochemistry of endo-(4’S)-3 was established to be (1R, 4S, 7R) and a reaction mechanism is proposed.