Organocatalytic enantioselective stereoablative hydroxylation of 3-halooxindoles: an effective method for the construction of enantioenriched 3-substituted 3-hydroxy-2-oxindoles.
3-Substituted oxindoles as electrophilic partners: An unprecedented method for the construction of hydroxylated 3-substituted oxindoles in high yields and excellent enantioselectivities through stereoablative hydroxylation of 3-halooxindoles with an organocatalyst has been developed. This process not only differs from the common convention of using 3-substituted oxindoles as nucleophiles, but also provides a viable entry to optically active 3-substituted 3-hydroxy-2-oxindoles (see scheme).
National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, PR China.
Yu-Hua
YH
Liao
Zhi-Jun
ZJ
Wu
Wen-Yong
WY
Han
Xiao-Mei
XM
Zhang
Wei-Cheng
WC
Yuan
D000470:Alkaloids / Q000737:chemistry*; D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D006900:Hydroxylation; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*; D000078183:Oxindoles; D013237:Stereoisomerism
D000470:Alkaloids; D006846:Hydrocarbons, Halogenated; D007211:Indoles; D010091:Oximes; D000078183:Oxindoles; C022960:2-oxindole