Organocatalytic Biomimetic Decarboxylative Aldol Reaction of Fluorinated β-Keto Acids with Unprotected Isatins
A facile asymmetric synthesis of fluorinated 3-hydroxyoxindoles through the biomimetic decarboxylative aldol reaction of fluorinated β-keto acids with unprotected isatins catalyzed by quinine-derived urea catalyst has been achieved. One of the features of this work is that the easily available α, α-difluoro/α-monofluoro-β-keto acids have been first applied in the enantioselective synthesis of fluorinated compounds as the masked fluoroenolates. Furthermore, the utility of this method was demonstrated by its ability to access a series of difluorinated 3-hydroxyoxindoles with up to 95% ee and monofluorinated 3-hydroxyoxindoles with up to 90 : 10 d.r. and 94% ee. (Figure presented.).
Li, Yin-Long,Wang, Xue-Lin,Xiao, Dan,Liu, Ming-Ying,Du, Yunfei,Deng, Jun
supporting information
p. 4147 - 4152
(2018/09/25)
2,2-Difluoro-1,3-diketones as gem-Difluoroenolate Precusors for Asymmetric Aldol Addition with N-Benzylisatins
2,2-Difluoro-1,3-diketones are introduced as gem-difluoroenolate precursors for the first example of an organocatalytic asymmetric aldol addition with N-benzylisatins to form 3-difluoroalkyl-3-hydroxyoxindoles. (Figure presented.).
Qian, Jinlong,Yi, Wenbin,Huang, Xin,Jasinski, Jerry P.,Zhang, Wei
p. 2811 - 2816
(2016/09/13)
Organocatalytic asymmetric synthesis of 3-difluoroalkyl 3-hydroxyoxindoles
We report the first example of highly enantioselective organocatalytic synthesis of 3-difluoroalkyl substituted 3-hydroxyoxindoles. The total synthesis of the difluoro analogue of convolutamydine E was achieved by this method.
Liu, Yun-Lin,Zhou, Jian
supporting information; scheme or table
p. 1919 - 1921
(2012/03/11)
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