Organocatalytic enantioselective construction of multi-functionalized spiro oxindole dienes.
A diastereo- and enantio-selective domino Michael-cyclization-tautomerization reaction of isatylidene malononitriles with α,α-dicyanoalkenes catalyzed by a cinchona alkaloid-derived bifunctional thiourea catalyst has been developed. A series of multi-functionalized spiro oxindole diene derivatives have been obtained in good to excellent yields (up to 97%) with good to excellent enantioselectivities (up to 96%) as well as good diastereoselectivities (up to 7.9 : 1). In addition, an anomalous temperature effect on the enantioselectivity has also been studied for this transformation.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China. wangxw@suda.edu.cn.
Xiao-Fei
XF
Huang
Ya-Fei
YF
Zhang
Zheng-Hang
ZH
Qi
Nai-Kai
NK
Li
Zhi-Cong
ZC
Geng
Kun
K
Li
Xing-Wang
XW
Wang
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole