Copper-Catalyzed Divergent Addition Reactions of Enoldiazoacetamides with Nitrones
Copper-Catalyzed Divergent Addition Reactions of Enoldiazoacetamides with Nitrones
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DOI：
10.1021/jacs.5b10860
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发表时间：
2016-01-13
影响因子：
15
通讯作者：
Doyle, Michael P.
中科院分区：
文献类型：
--
作者：
Cheng, Qing-Qing;Yedoyan, Julietta;Doyle, Michael P.
研究了烯诺二氮乙酰胺与硝基酮的催化控制的发散加成反应。以四氟硼酸铜/双恶唑啉配合物为催化剂，在异常温和的条件下，以优异的产率和对映选择性实现了[3+3]-环加成反应，首次实现了高对映选择性的碱金属催化乙烯-碳转化。当催化剂改为三酸铜时，在其他条件相同的情况下，曼尼希加成产物的产率很高，几乎是排他性的。
Catalyst-controlled divergent addition reactions of enoldiazoacetamides with nitrones have been developed. By using copper(I) tetrafluoroborate/bisoxazoline complex as the catalyst, a [3+3]-cycloaddition reaction was achieved with excellent yield and enantioselectivity under exceptionally mild conditions, which represents the first highly enantioselective base-metal-catalyzed vinyl-carbene transformation. When the catalyst was changed to copper(I) triflate, Mannich addition products were formed in high yields with near exclusivity under otherwise identical conditions.