The Journal of Organic Chemistry

Asymmetric hetero Diels-Alder reaction of. alpha.-alkoxy aldehydes with activated dienes. The scope of Lewis acid chelation-controlled cycloadditions

MM Midland, RW Koops

Index: Midland, M. Mark; Koops, Roger W. Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 5058 - 5065

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Citation Number: 83

Abstract

The cycloaddition reactions of various a-alkoxy aldehydes with 1, 3-dimethoxy-1- [(trimethylsilyl) oxy]-1, 3-butadiene (Brassard's diene, 2) were performed under the Lewis acid catalysis of Eu (hfc),, magnesium dibromide, or diethylaluminum chloride. Moderate to high diastereoselectivities were observed with Eu (hfc), and magnesium dibromide. Evidence from reactions of E~(hfc)~ and magnesium dibromide catalysis indicated a ...

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