Beck Barbara, Picard Anne, Herdtweck Eberhardt, Dömling Alexander
Morphochem AG, Gmunderstr. 37-37a, 81379 Munich, Germany.
Org Lett. 2004 Jan 8;6(1):39-42. doi: 10.1021/ol035787n.
[reaction: see text] By combining a Ugi four-component reaction of isocyanides, phosphonoacetic acids, primary amines, and glyoxals or alternatively 3-keto aldehydes with a subsequent Wittig ring-closing reaction (using the Horner/Wadsworth/Emmons variant (HWE)), highly substituted 5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylic acid amides and 6-oxo-1,2,3,6-tetrahydro-pyridine-2-carboxylic acid amides can be assembled, respectively. The corresponding tandem of a Passerini reaction on 3-keto aldehydes and subsequent Wittig ring closure does not afford the expected six-membered 6-oxo-3,6-dihydro-2H-pyran-2-carboxylic acid amides but instead leads to the formation of 4-oxo-pent-2-enoic acid amides via an elimination route.
[反应：见正文] 通过将异腈、膦酰基乙酸、伯胺和乙二醛或3-氧代醛进行Ugi四组分反应，随后进行维蒂希环化反应（使用霍纳/沃兹沃思/埃蒙斯变体（HWE）），可以分别组装出高度取代的5-氧代-2,5-二氢-1H-吡咯-2-羧酸酰胺和6-氧代-1,2,3,6-四氢吡啶-2-羧酸酰胺。在3-氧代醛上进行帕瑟里尼反应并随后进行维蒂希环化的相应串联反应，并没有得到预期的六元6-氧代-3,6-二氢-2H-吡喃-2-羧酸酰胺，而是通过消除途径导致形成4-氧代-戊-2-烯酸酰胺。
