A facile approach for the asymmetric synthesis of oxindoles with a 3-sulfenyl-substituted quaternary stereocenter.
With the employment of a threonine-incorporating multifunctional catalyst 9, Michael addition of 3-sulfenyloxindoles to nitroolefins proceeded stereoselectively, leading to the formation of oxindoles with a 3-sulfenyl-substituted quaternary center in excellent yields, and with high diastereoselectivities and excellent enantioselectivities.
Department of Chemistry and Medicinal Chemistry Program, Life Sciences Institute, National University of Singapore , 3 Science Drive 3, Republic of Singapore 117543.
Xiaowei
X
Dou
Bo
B
Zhou
Weijun
W
Yao
Fangrui
F
Zhong
Chunhui
C
Jiang
Yixin
Y
Lu
D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D000078183:Oxindoles; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D007211:Indoles; D009574:Nitro Compounds; D000078183:Oxindoles; D013438:Sulfhydryl Compounds; C022960:2-oxindole