Abstract
The Lewis acid catalyzed cycloaddition reactions of α-benzyloxy imines (RCH(OCH 2 C 6 H 5 6)CH=NCH 2 C 6 H 5 ) were investigated using 1,3-dimethoxy-1-[(trimethylsilyl)oxy]-1,3-butadiene. The observed diastereoselectivity was dependent on both the Lewis acid and substrate structure. Strong Lewis acids such as diethylaluminum chloride (DEAC) exhited moderate to good success in promoting the cycloaddition reaction. When DEAC was used as the Lewis acid, the diastereoselectivity was also dependent on the stoichiometry of the Lewis acid to the substrate
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