Palladium-Catalyzed Domino Carbopalladation/5-exo-Allylic Amination of α-Amino Allenamides: An Efficient Entry to Enantiopure Imidazolidinones
Palladium-Catalyzed Domino Carbopalladation/5-exo-Allylic Amination of α-Amino Allenamides: An Efficient Entry to Enantiopure Imidazolidinones
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DOI：
10.1021/ol900171g
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发表时间：
2009-04-02
期刊：
影响因子：
5.2
通讯作者：
Sottocornola, Silvia
中科院分区：
文献类型：
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作者：
Beccalli, Egle M.;Broggini, Gianluigi;Sottocornola, Silvia
通过碳钯化/外环化过程将α-氨基酸的丙二酰胺转化为对映体纯的2-乙烯基咪唑烷-4-酮。产物在2.5：1-5.5：1的dr范围内得到，ee值为94-99%，相同底物经钯催化羰基环化得到烯酮结构。从适当取代的丙二烯酰胺，分子内carbopalladation，然后分子内胺化产生三环稠环咪唑烷酮。
Allenamides of alpha-amino acids were converted into enantiopure 2-vinylimidazolidin-4-ones by a carbopalladation/exo-cyclization process. The products were obtained in 2.5:1-5.5:1 dr, with 94-99% ee. The palladium-catalyzed carbonylative cyclization of the same substrates afforded enone structures. Starting from properly substituted allenamides, an intramolecular carbopalladation followed by intramolecular amination gave rise to tricyclic fused-ring imidazolidinones.