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Catalytic Enantioselective and Diastereoselective Allylic Alkylation with Fluoroenolates: Efficient Access to C3‐Fluorinated and All‐Carbon Quaternary Oxindoles
Author(s) -
Balaraman Kaluvu,
Wolf Christian
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201608752
Subject(s) - enantioselective synthesis , tsuji–trost reaction , regioselectivity , vicinal , alkylation , chirality (physics) , allylic rearrangement , stereoselectivity , chemistry , quaternary carbon , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
Synthetically versatile 3,3‐disubstituted fluorooxindoles exhibiting vicinal chirality centers were obtained in high yields and with excellent enantio‐, diastereo‐, and regioselectivity through catalytic asymmetric fluoroenolate alkylation with allylic acetates. The reaction proceeds under mild conditions and can be scaled up without compromising the asymmetric induction. The unique synthetic usefulness of the products is highlighted by the incorporation of additional functionalities and the formation of 3‐fluorinated oxindoles exhibiting an array of four adjacent centers of chirality. A new C−F bond functionalization path that provides unprecedented possibilities for the stereoselective generation of a chiral quaternary carbon center in the alkaloid scaffold is introduced.