Enantioselective Synthesis of Indolizidines Bearing Quaternary Substituted Stereocenters via Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition of Alkenyl Isocyanates and Terminal Alkynes

作者: Ernest E. Lee , Tomislav Rovis

DOI: 10.1021/OL800086S

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摘要: An enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters by way a rhodium-catalyzed [2+2+2] cycloaddition alkenyl isocyanates and terminal alkynes is described. The reaction provides lactam products using aliphatic alkynes, whereas aryl give rise to vinylogous amide products. Through modification the phosphoramidite ligand, high levels enantioselectivity, regioselectivity, product selectivity are obtained for both

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