One-pot cross-coupling of N-acyl N,O-acetals with alpha,beta-unsaturated compounds.
The synergistic action of BF(3).OEt(2) and SmI(2) allowed a series of intermolecular cross-couplings of readily available N-acyl N,O-acetals with alpha,beta-unsaturated compounds to be performed in high yields, which was applied to the stereoselective synthesis of pyrrolizidine alkaloid (+)-xenovenine.
Xiang
Yong-Gang
YG
Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, PR China.
Wang
Xiang-Wu
XW
Zheng
Xiao
X
Ruan
Yuan-Ping
YP
Huang
Pei-Qiang
PQ
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D012493:Samarium / Q000737:chemistry; D013237:Stereoisomerism
D000080:Acetals; D001880:Boranes; D007454:Iodides; D011763:Pyrrolizidine Alkaloids; C545571:xenovenine; C101707:boron trifluoride etherate; D012493:Samarium; C409809:samarium diiodide