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Issue 10, 2014
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Palladium-catalyzed trifluoroacetate-promoted mono-arylation of the β-methyl group of alanine at room temperature: synthesis of β-arylated α-amino acids through sequential C–H functionalization

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Abstract

We report a highly efficient and practical protocol for palladium-catalyzed N-quinolylcarboxamide (AQ)-directed arylation of the unactivated β-C(sp3)–H bonds of alanine with aryl iodides at room temperature. For the first time, a broad range of easily accessible aryl iodides can be installed onto the β-methyl group of AQ-coupled phthaloyl alanine mono-selectively, providing both natural and unnatural aromatic α-amino acids. Access to these mono-arylated compounds enables subsequent AQ-directed diastereoselective C–H functionalization, allowing the preparation of various β-disubstituted aromatic α-amino acids in a programmable manner.

Graphical abstract: Palladium-catalyzed trifluoroacetate-promoted mono-arylation of the β-methyl group of alanine at room temperature: synthesis of β-arylated α-amino acids through sequential C–H functionalization

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Article information


Submitted
26 May 2014
Accepted
16 Jun 2014
First published
17 Jun 2014

Chem. Sci., 2014,5, 3952-3957
Article type
Edge Article

Palladium-catalyzed trifluoroacetate-promoted mono-arylation of the β-methyl group of alanine at room temperature: synthesis of β-arylated α-amino acids through sequential C–H functionalization

B. Wang, W. A. Nack, G. He, S. Zhang and G. Chen, Chem. Sci., 2014, 5, 3952
DOI: 10.1039/C4SC01545B

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