Asymmetric organocatalysis of 4+3 cycloaddition reactions
Asymmetric organocatalysis of 4+3 cycloaddition reactions
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DOI：
10.1021/ja029058z
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发表时间：
2003-02-26
影响因子：
15
通讯作者：
Kirchhoefer, P
中科院分区：
文献类型：
--
作者：
Harmata, M;Ghosh, SK;Kirchhoefer, P
用手性仲胺、三氟乙酸和二烯处理几种4-trialkylsilyloxypentadienals导致形成4 + 3环加成产物，其是对映体富集的。这代表了4 + 3环加成反应的不对称有机催化的第一个例子。2，5-二甲基呋喃与4-三甲基硅氧基-2，4-双烯醛在催化量的手性胺和酸的存在下反应，以64%的产率得到单一非对映体的环加成物，对映体过量为89%。
Treatment of several 4-trialkylsilyloxypentadienals with a chiral secondary amine, trifluoroacetic acid, and a diene resulted in the formation of 4 + 3 cycloaddition products, which were enantiomerically enriched. This represents the first examples of the asymmetric organocatalysis of the 4 + 3 cycloaddition reaction. 2,5-Dimethylfuran reacted with 4-trimethylsilyloxy-2,4-pentadienal in the presence of catalytic amounts of chiral amine and acid to afford a cycloadduct in 64% yield as a single diastereomer with an enantiomeric excess of 89%.