Catalytic asymmetric construction of spiro[pyrrolidine-2,3'-oxindole] scaffolds through chiral phosphoric acid-catalyzed 1,3-dipolar cycloaddition involving 3-amino oxindoles.
The catalytic asymmetric three-component 1,3-dipolar cycloaddition of 3-amino oxindoles with aldehydes and nitroolefins under the catalysis of a chiral phosphoric acid is reported. The reaction provides a facile approach to synthesize a diverse array of spiro[pyrrolidine-2,3'-oxindoles] in high yields with excellent diastereo- and enantioselectivities under mild conditions.
State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology, Dalian 116024, P. R. China. bmwang@dlut.edu.cn.
Guodong
G
Zhu
Baomin
B
Wang
Xiaoze
X
Bao
Huanrui
H
Zhang
Qian
Q
Wei
Jingping
J
Qu
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009595:Nitroparaffins / Q000737:chemistry; D000078183:Oxindoles; D010756:Phosphoric Acids / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D007211:Indoles; D009595:Nitroparaffins; D000078183:Oxindoles; D010756:Phosphoric Acids; D013141:Spiro Compounds; C000606610:spiro(pyrrolidine-2,3'-oxindole); C022960:2-oxindole; C030242:phosphoric acid