The organocatalytic asymmetric Neber reaction for the enantioselective synthesis of spirooxindole 2H-azirines.
The asymmetric Neber reaction of 3-O-sulfonyl ketoxime, in situ generated from isatin ketoxime and sulfonyl chloride, for the synthesis of chiral spirocyclic oxindole compounds is reported. With the developed protocol, a range of chiral spirooxindole 2H-azirines could be obtained in good to excellent yields and up to a 92 : 8 enantiomeric ratio by using (DHQD)2PHAL as the catalyst. This methodology is the only example of the catalytic asymmetric construction of spirooxindole 2H-azirine compounds.
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. xuxy@cioc.ac.cn yuanwc@cioc.ac.cn and Institute for Advanced Study, Chengdu University, Chengdu 610106, China and University of Chinese Academy of Sciences, Beijing 100049, China.
Jian-Qiang
JQ
Zhao
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. xuxy@cioc.ac.cn yuanwc@cioc.ac.cn and University of Chinese Academy of Sciences, Beijing 100049, China.
Deng-Feng
DF
Yue
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. xuxy@cioc.ac.cn yuanwc@cioc.ac.cn.
Xiao-Mei
XM
Zhang
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. xuxy@cioc.ac.cn yuanwc@cioc.ac.cn.
Xiao-Ying
XY
Xu
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. xuxy@cioc.ac.cn yuanwc@cioc.ac.cn.
Wei-Cheng
WC
Yuan
D001389:Azirines / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D001389:Azirines; D013141:Spiro Compounds