The reaction of tributyltinenolates with α-halogenoketones gave substituted furans which were not derived from the normal cross-coupling products, 1,4-diketones, but were formed instead through addition of the tin enolate to the α-halogenoketones.
Synthesis of Substituted Acetylenic Epoxides Followed by Indium-Catalyzed Rearrangement to 2,3,5-Trisubstituted Furans
作者:Jun Yong Kang、Brian T. Connell
DOI:10.1021/jo2001353
日期:2011.4.1
Syntheses of various aromatic and aliphatic 2,3,5-trisubstituted furansfrom acetylenic epoxides are described. These epoxides are directly prepared by nucleophilic ring closure of propargylic alkoxides generated by lithium acetylide addition to α-haloketones.