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Synfacts 2017; 13(05): 0493
DOI: 10.1055/s-0036-1590253
DOI: 10.1055/s-0036-1590253
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Palladium-Catalyzed Asymmetric C–H Functionalizations of Isobutanamides
Wu Q.-F.
Shen P.-X.
He J.
Wang X.-B.
Zhang F.
Shao Q.
Zhu R.-Y.
Mapelli C.
Qiao JX.
Poss MA.
Yu J.-Q.
* The Scripps Research Institute, La Jolla and Bristol-Myers Squibb Company, Princeton, USA
Formation of α-Chiral Centers by Asymmetric β-C(sp3)–H Arylation, Alkenylation, and Alkynylation.
Science 2017;
355: 499-503
Formation of α-Chiral Centers by Asymmetric β-C(sp3)–H Arylation, Alkenylation, and Alkynylation.
Science 2017;
355: 499-503
Further Information
Publication History
Publication Date:
18 April 2017 (online)
Key words
palladium catalysis - C–H functionalization - arylation - alkenylation - alkynylation - isobutanamides
Significance
Desymmetrization of isopropyl moieties has remained an unanswered challenge. The authors have developed new ligands for the formation of a chiral center at the α-position of isobutyric acid derivatives through β-C(sp3)–H functionalization.
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Comment
This palladium-catalyzed protocol promotes an asymmetric β-C(sp3)–H arylation, alkenylation, or alkynylation to form a chiral center at the α-position of a range of isobutyric acid derivatives with moderate yields and excellent enantioselectivities.
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