In:
Angewandte Chemie, Wiley, Vol. 129, No. 20 ( 2017-05-08), p. 5643-5647
Abstract:
Despite the burgeoning demand for fluorine‐containing chemical entities, the construction of CF 3 ‐containing stereogenic centers has remained elusive. Herein, we report the strategic merger of Cu I /base‐catalyzed enolization of an α‐CF 3 amide and Pd 0 ‐catalyzed allylic alkylation in an enantioselective manner to deliver chiral building blocks bearing a stereogenic carbon center connected to a CF 3 , an amide carbonyl, and a manipulable allylic group. The phosphine complexes of Cu I and Pd 0 engage in distinct catalytic roles without ligand scrambling to render the dual catalysis operative to achieve asymmetric α‐allylation of the amide. The stereoselective cyclization of the obtained α‐CF 3 ‐γ,δ‐unsaturated amides to give tetrahydropyran and γ‐lactone‐fused cyclopropane skeletons highlights the synthetic utility of the present catalytic method as a new entry to non‐racemic CF 3 ‐containing compounds.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v129.20
DOI:
10.1002/ange.201702113
Language:
English
Publisher:
Wiley
Publication Date:
2017
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