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Synfacts 2017; 13(05): 0493
DOI: 10.1055/s-0036-1590253
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Asymmetric C–H Functionalizations of Isobutanamides

Authors

    Rezensent(en):

  • Hisashi Yamamoto

  • Wataru Muramatsu

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
CrossrefPubMedSuche in Google Scholar
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Publikationsverlauf

Publikationsdatum:
18. April 2017 (online)

 
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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.


 

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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