ASYMMETRIC HETERO-DIELS-ALDER REACTION OF ALPHA-ALKOXY ALDEHYDES WITH ACTIVATED DIENES - THE SCOPE OF LEWIS ACID CHELATION-CONTROLLED CYCLOADDITIONS

被引：76
作者：
MIDLAND, MM
KOOPS, RW
机构：
[1] Department of Chemistry, University of California,Riverside, Riverside
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 17期
关键词：
D O I：
10.1021/jo00304a018
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The cycloaddition reactions of various α-alkoxy aldehydes with l,3-dimethoxy-l-[(trimethylsilyl)oxy]-l,3-butadiene (Brassard's diene, 2) were performed under the Lewis acid catalysis of Eu(hfc)3, magnesium dibromide, or diethylaluminum chloride. Moderate to high diastereoselectivities were observed with Eu(hfc)3 and magnesium dibromide. Evidence from reactions of Eu(hfc)3 and magnesium dibromide catalysis indicated a possible “chelation-control” pathway. Lewis acid catalysis from diethylaluminum chloride provided products with moderate to high diastereoselectivity. The mechanistic pathway with catalysis by diethylaluminum chloride was less clear. A possible mechanism based upon a “Cram” addition is considered. © 1990, American Chemical Society. All rights reserved.
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页码：5058 / 5065
页数：8
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