Highly diastereo- and enantioselective construction of a spiro[cyclopenta[b]indole-1,3'-oxindole] scaffold via catalytic asymmetric formal [3+2] cycloadditions.
An organocatalytic asymmetric formal [3+2] cycloaddition of isatin-derived 3-indolylmethanol with 3-methyl-2-vinylindole has been established, leading to highly stereoselective construction of a spiro[cyclopenta[b]indole-1,3'-oxindole] scaffold with the concomitant creation of three contiguous stereogenic centers (72-99% yield, all >95 : 5 dr, 90-98% ee), one of which is an all-carbon quaternary stereogenic center.
School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116, China. fshi@jsnu.edu.cn.
Wei
W
Tan
Xin
X
Li
Yu-Xin
YX
Gong
Meng-Di
MD
Ge
Feng
F
Shi
D002384:Catalysis; D061565:Cycloaddition Reaction; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D007211:Indoles; D013141:Spiro Compounds