Highly stereoselective catalytic conjugate addition of acyl anion equivalent to nitroolefins
Highly stereoselective catalytic conjugate addition of acyl anion equivalent to nitroolefins
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DOI：
10.1039/c1sc00678a
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发表时间：
2012-02
期刊：
影响因子：
8.4
通讯作者：
D. Uraguchi;Y. Ueki;T. Ooi
中科院分区：
文献类型：
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作者：
D. Uraguchi;Y. Ueki;T. Ooi
利用超分子组装的手性芳氧芳氢氧化四氨基膦1a·[2a]2作为催化剂，实现了2-未取代吖内酯3与多种硝基烯烃4的高对映选择性共轭加成反应.这一成就的关键是1·[2]n型分子缔合的极性依赖性和邻近的芳基氢氧化物2作为质子供体的关键作用。本方法为制备包括β2-氨基酸在内的各种光学活性氨基羰基化合物提供了一条有吸引力的途径。
Highly enantioselective conjugate addition of 2-unsubstituted azlactone 3 to various nitroolefins 4 was accomplished by the selective utilization of supramolecularly assembled, chiral tetraaminophosphonium aryloxide–arylhydroxide 1a·[2a]2 as a requisite catalyst. The key to this achievement is the polarity dependence of the molecular associations of type 1·[2]n and the crucial role of the proximal arylhydroxide 2 as a proton donor. The present method offers an attractive route to various optically active amino carbonyl compounds including β2-amino acids.