Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 5, Pages 1390-1395Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608752
Keywords
alkaloids; homogeneous catalysis; organofluorines; quaternary chiral centers; synthetic methods
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Funding
- NIH [R15GM106260]
- American Chemical Society Petroleum Research Fund [PRF52737ND]
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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.
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