Highly enantioselective construction of spiro[4H-pyran-3,3'-oxindoles] through a domino Knoevenagel/Michael/cyclization sequence catalyzed by cupreine.
The first enantioselective organocatalytic two- and three-component reactions via a domino Knoevenagel/Michael/cyclization sequence with cupreine as catalyst have been developed. A wide range of optically active spiro[4H-pyran-3,3'-oxindoles] were obtained in excellent yields (up to 99%) with good to excellent enantioselectivities (up to 97%) from simple and readily available starting materials under mild reaction conditions. These heterocyclic spirooxindoles will provide promising candidates for chemical biology and drug discovery.
Chen
Wen-Bing
WB
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
Wu
Zhi-Jun
ZJ
Pei
Qing-Lan
QL
Cun
Lin-Feng
LF
Zhang
Xiao-Mei
XM
Yuan
Wei-Cheng
WC
D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D000078183:Oxindoles; D011804:Quinolines / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007211:Indoles; D000078183:Oxindoles; D011804:Quinolines; D013141:Spiro Compounds; C022960:2-oxindole; C552577:cupreine