The asymmetric synthesis of CF3-containing spiro[pyrrolidin-3,2'-oxindole] through the organocatalytic 1,3-dipolar cycloaddition reaction.
A new strategy for the construction of optically active 5'-CF3 spiro[pyrrolidin-3,2'-oxindole] was described. A series of unprecedented 1,3-dipoles were obtained by condensation of CF3CH2NH2 with isatins. The 1,3-dipolar cycloaddition reactions of these ketimines with enals gave the products bearing four contiguous stereogenic centers in excellent yields, diastereoselectivities and enantioselectivities.
Department of Pharmacology, Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000, China. wangkr@lzu.edu.cn wangrui@lzu.edu.cn.
Mingxia
M
Ma
Yuanyuan
Y
Zhu
Quantao
Q
Sun
Xiaoyuan
X
Li
Jinhuan
J
Su
Long
L
Zhao
Yanyan
Y
Zhao
Shuai
S
Qiu
Wenjin
W
Yan
Kairong
K
Wang
Rui
R
Wang
D002384:Catalysis; D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C575768:spiro(pyrrolidin-3,2'-oxindole)