In:
Angewandte Chemie, Wiley, Vol. 131, No. 5 ( 2019-01-28), p. 1461-1466
Abstract:
Demonstrated herein is the construction of trifluoromethylated quaternary carbon centers by an asymmetric radical transformation. Enantioenriched trifluoromethylated oxindoles were accessed using a hypervalent iodine‐based trifluoromethyl transfer reagent in combination with a magnesium Lewis acid catalyst and PyBOX‐type ligands to achieve up to 99 % ee and excellent chemical yields. Mechanistic studies were performed by experimental and computational methods and suggest a single‐electron transfer induced S N 2‐type mechanism. This example is thereby the first report on the construction of enantioenriched trifluoromethylated carbon centers using hypervalent iodine‐based reagents proceeding through such a reaction pathway.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.201812793
Language:
English
Publisher:
Wiley
Publication Date:
2019
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505868-5
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514305-6
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505872-7
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1479266-7
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506259-7
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