Asymmetric construction of nitrogen-containing [2.2.2] bicyclic scaffolds using N-( p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide.
Asymmetric construction of nitrogen-containing [2.2.2] bicyclic scaffolds using N-( p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide.
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DOI：
10.1021/jo9009062
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发表时间：
2009-08
期刊：
影响因子：
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通讯作者：
Hua Yang;R. Carter
中科院分区：
文献类型：
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作者：
Hua Yang;R. Carter
研究了对十二烷基苯磺酰胺修饰的脯氨酸催化合成对映体富集的异奎宁环和双环[2.2.2]辛烷。已经探索了一系列芳香族亚胺用于形成具有高水平的对映体选择性和非对映体选择性的异奎宁环，强烈地有利于外消旋产物。还探索了一系列脂肪族亚胺，它们通过一种新型机制途径以高水平的对映体选择性和非对映体选择性提供双环[2.2.2]辛烷，有利于内产物。
An organocatalyzed approach to enantioenriched isoquinuclidines and bicyclo[2.2.2]octanes via a p-dodecylphenylsulfonamide-modified proline catalyst has been developed. A series of aromatic imines have been explored for the formation of isoquinuclidines with high levels of enantioselectivity and diastereoselectivity, strongly favoring the exo product. A series of aliphatic imines has also been explored, which provide access to bicyclo[2.2.2]octanes through a novel mechanistic pathway in high levels of enantioselectivity and diastereoselectivity, favoring the endo product.