Enantioselective construction of 2,5-dihydropyrrole skeleton with quaternary stereogenic center via catalytic asymmetric 1,3-dipolar cycloaddition involving α-arylglycine esters.
A catalytic asymmetric construction of synthetically and biologically important 2,5-dihydropyrrole scaffolds with concomitant creation of multiple chiral carbon centers including one quaternary stereogenic center in high yields (up to 99%) and excellent enantioselectivities (up to 99% ee) has been established via an organocatalytic 1,3-dipolar cycloaddition using α-arylglycine esters as azomethine precursors. Moreover, a detailed investigation has been performed on the catalytic asymmetric 1,3-dipolar cycloadditions of α-arylglycine ester-generated azomethine ylides with alkynes, providing an efficient way to simultaneously access both 2,5-dihydropyrrole diastereomers in good enantioselectivities.
School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, China. fshi@jsnu.edu.cn
Feng
F
Shi
Gui-Juan
GJ
Xing
Wei
W
Tan
Ren-Yi
RY
Zhu
Shujiang
S
Tu
D002384:Catalysis; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D004952:Esters; D011758:Pyrroles; D005998:Glycine