Amplification of asymmetric induction in sequential reactions of bis-diazoacetates catalyzed by chiral dirhodium(II) carboxamidates
Amplification of asymmetric induction in sequential reactions of bis-diazoacetates catalyzed by chiral dirhodium(II) carboxamidates
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DOI：
10.1021/ol0520121
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发表时间：
2005-10-27
期刊：
影响因子：
5.2
通讯作者：
Bappert, E
中科院分区：
文献类型：
--
作者：
Doyle, MP;Wang, YH;Bappert, E
[图表]报道了使用手性氨甲酰二铑（II）催化剂的双重氮乙酸酯的两个连续的分子内碳氢插入或环丙烷化反应。初始金属卡宾转化形成过量的一种对映异构体，其与第二转化一起进一步增强立体控制（动力学扩增）。产物形成的非对映选择性和对映选择性由催化剂控制。
[GRAPHICS]Two sequential intramolecular carbon-hydrogen insertion or cyclopropa nation reactions of bis-diazoacetates using chiral dirhodium(II) carboxamidate catalysts are reported. The initial metal carbene transformation forms an excess of one enantiomer that with the second transformation further enhances stereocontrol (kinetic amplification). Diastereoselectivity and enantioselectivity for product formation are controlled by the catalyst.