Diastereo- and Enantioselective Construction of 3,3'-Pyrrolidinyldispirooxindole Framework via Catalytic Asymmetric 1,3-Dipolar Cycloadditions.
The first catalytic enantioselective construction of a 3,3'-pyrrolidinyldispirooxindole scaffold has been established via organocatalytic asymmetric 1,3-dipolar cycloadditions of isatin-derived azomethine ylides with methyleneindolinones, which afforded structurally complex bis-spirooxindoles containing three contiguous and two quaternary stereogenic centers in generally high yields (up to 99%) and excellent diastereo- and enantioselectivities (up to >95:5 dr, 98% ee). This reaction also provides a good example for the application of catalytic asymmetric 1,3-dipolar cycloadditions in constructing enantioenriched bis-spirooxindole frameworks with structural complexity and rigidity.
Wei
W
Dai
Xiao-Li
XL
Jiang
‡School of Chemistry and Chemical Engineering, Xuzhou Institute of Technology, Xuzhou 221008, China.
Qiong
Q
Wu
Feng
F
Shi
Shu-Jiang
SJ
Tu
D002384:Catalysis; D061565:Cycloaddition Reaction; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
C000605070:3,3'-Pyrrolidinyldispirooxindole; D007211:Indoles; D000078183:Oxindoles; D011759:Pyrrolidines; D013141:Spiro Compounds; D007510:Isatin