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Note | Regular issue | Vol 60, No. 9, 2003, pp.2141-2145
Published online, 18th August, 2003
DOI: 10.3987/COM-03-9835
Metal Chelations in Asymmetric Diels-Alder Reaction

Kyoo-Hyun Chung,* Chan-Kook Chu, and Min-Ho Chang

*Department of Chemistry, Inha University, 253, Yonghyundong Namgu, Inchon 402-751, Korea

Abstract

In the presence of chiral catalysts, Diels-Alder reaction of a N-acryloyl chiral dienophile with cyclopentadiene gave the corresponding endo norbornenecarboxamide with high diastereoselectivity. In the reaction, 8-membered chelation was effective enough to distinguish transoid and cisoid conformation in the presence of divalent Lewis acid catalysts, such as TiCl4.