Enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes
Enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes
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DOI：
10.1021/ol800086s
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发表时间：
2008-03-20
期刊：
影响因子：
5.2
通讯作者：
Rovis, Tomislav
中科院分区：
文献类型：
--
作者：
Lee, Ernest E.;Rovis, Tomislav
通过铑催化的取代链烯基异氰酸酯与末端炔的[2 + 2 + 2]环加成反应，对映选择性合成了带有季取代立构中心的中氮茚。该反应使用脂族炔提供内酰胺产物，而芳基炔产生乙烯基乙酰胺产物。通过修饰亚磷酰胺配体，两种产物都获得了高水平的对映选择性、区域选择性和产物选择性。
An enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters by way of a rhodium-catalyzed [2 + 2 + 2] cycloaddition of substituted alkenyl isocyanates and terminal alkynes is described. The reaction provides lactam products using aliphatic alkynes, whereas aryl alkynes give rise to vinylogous amide products. Through modification of the phosphoramidite ligand, high levels of enantioselectivity, regioselectivity, and product selectivity are obtained for both products.