Asymmetric quadruple aminocatalytic domino reactions to fused carbocycles incorporating a spirooxindole motif.
The efficient assembly of hydroindane derivatives incorporating a spirooxindole motif was realized via a new three-component domino reaction of (E)-4-(1-methyl-2-oxoindolin-3-ylidene)-3-oxobutanoates and two molecules of alpha,beta-unsaturated aldehydes under quadruple iminium-enamine-iminium-enamine catalysis. The complex products bearing six contiguous stereogenic centers were obtained in excellent stereoselectivities (96->99% ee, >99% de).
Jiang
Kun
K
Key Laboratory of Drug-Targeting and Drug Delivery System of Education Ministry, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Jia
Zhi-Jun
ZJ
Yin
Xiang
X
Wu
Li
L
Chen
Ying-Chun
YC
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D007189:Indans; D007211:Indoles; D013141:Spiro Compounds