Department of Applied Chemistry, National Chiao Tung University , 1001, Ta-Hsueh Road, Hsinchu 30010, Taiwan, R.O.C.
Org Lett. 2014 Nov 7;16(21):5792-5. doi: 10.1021/ol502879c. Epub 2014 Oct 22.
Multicomponent reactions of phosphines, diynedioates, and aryl aldehydes have been demonstrated, providing trisubstituted furans appending reactive phosphorus ylides, through cumulated trienoates as key intermediates. The proposed trienoate intermediates, 1,5-dipolar species formed via nucleophilic α-attack of phosphines toward diynedioates (α-addition-δ-evolvement of an anion, abbreviated αAδE), undergo addition to aryl aldehydes followed by 5-endo-dig cyclization, proton transfer, and resonance to give trisubstituted furans. Furthermore, the phosphorus ylides are oxidized to α-keto ester furans and utilized as Wittig reagents.
已经证明了膦、二炔二酸酯和芳醛的多组分反应，通过累积的三烯酸酯作为关键中间体，提供了连接反应性磷叶立德的三取代呋喃。所提出的三烯酸酯中间体是通过膦对二炔二酸酯的亲核α-进攻（α-加成-δ-阴离子演变，简称αAδE）形成的 1,5-二极体，与芳醛加成，然后进行 5-endo-dig 环化、质子转移和共振，得到三取代呋喃。此外，磷叶立德被氧化为α-酮酯呋喃，并用作维蒂希试剂。
