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Angew Chem Int Ed Engl. 2017 Feb 1;56(6):1506-1509. doi: 10.1002/anie.201610580. Epub 2017 Jan 3.

Ligand-Enabled β-C-H Arylation of α-Amino Acids Without Installing Exogenous Directing Groups.

Author information

1
Department of Chemistry, The Scripps Research Institute (TSRI), 10550 North Torrey Pines Road, La Jolla, CA, 92037, USA.
2
Chemical and Synthetic Development, Bristol-Myers Squibb, 1 Squibb Drive, New Brunswick, NJ, 08903, USA.

Abstract

Herein we report acid-directed β-C(sp3 )-H arylation of α-amino acids enabled by pyridine-type ligands. This reaction does not require the installation of an exogenous directing group, is scalable, and enables the preparation of Fmoc-protected unnatural amino acids in three steps. The pyridine-type ligands are crucial for the development of this new C(sp3 )-H arylation.

KEYWORDS:

C−H activation; amino acids; arylation; palladium; pyridine ligands

PMID:
28052530
PMCID:
PMC5302090
DOI:
10.1002/anie.201610580
[Indexed for MEDLINE]
Free PMC Article

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