Highly enantioselective Ag(i)-catalyzed [3 + 2] cycloaddition of azomethine ylides.
A highly reactive Ag(I)-catalyzed [3 + 2] cycloaddition of azomethine ylides is founded using AgOAc as the catalytic precursor and phosphines as ligands. Using a new bis-ferrocenyl amide phosphine (FAP) as the ligand, we found that high enantioselectivities (up to 97% ee) have been achieved in the [3 + 2] cycloaddition of azomethine ylides. Up to four stereogenic centers can be established in this multicomponent coupling reaction from readily available materials such as aldehydes, aminoesters, and dipolarophiles.
Longmire
James M
JM
Department of Chemistry, 152 Davey Laboratory, The Pennsylvania State University, University Park 16802, USA.
Wang
Bin
B
Zhang
Xumu
X
D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008298:Maleates / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis*; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
D001391:Azo Compounds; D008298:Maleates; D011759:Pyrrolidines; D012834:Silver; C004780:dimethyl maleate