Sc(OTf)3-mediated 1,3-dipolar cycloaddition-ring cleavage-rearrangement: a highly stereoselective access to Z-β-enaminonitriles.
A novel and highly stereoselective synthesis of Z-β-enaminonitriles from azides and α,β-unsaturated nitriles is reported. The reaction proceeds via a 1,3-dipolar cycloaddition-ring cleavage-rearrangement cascade mediated by a catalytic amount of Sc(OTf)3. A plausible reaction mechanism for this process is depicted.
Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), School of Chemistry & Chemical Engineering of Guangxi Normal University, Guilin 541004, People's Republic of China. whengshan@163.com panym2013@hotmail.com.
Ying-chun
YC
Wang
Yu-yang
YY
Xie
Xian-chun
XC
Tan
Heng-shan
HS
Wang
Ying-ming
YM
Pan
D061565:Cycloaddition Reaction; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
D009570:Nitriles