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Issue 10, 2015
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Palladium-catalyzed alkylation of unactivated C(sp3)–H bonds with primary alkyl iodides at room temperature: facile synthesis of β-alkyl α-amino acids

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Abstract

An efficient protocol for the synthesis of β-alkyl α-amino acids via palladium-catalyzed β-C(sp3)–H alkylation of aminoquinoline-coupled phthaloyl alanine is developed. The new TFA-promoted reaction conditions provide excellent C–H alkylation reactivity with alkyl iodides bearing moderately electron-withdrawing groups at room temperature. A range of β-alkyl α-amino acid products, including some difficult to access by other means, can be quickly prepared from readily available primary alkyl iodides and alanine precursors.

Graphical abstract: Palladium-catalyzed alkylation of unactivated C(sp3)–H bonds with primary alkyl iodides at room temperature: facile synthesis of β-alkyl α-amino acids

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Supplementary files

Article information


Submitted
06 Apr 2015
Accepted
22 Jul 2015
First published
23 Jul 2015

Org. Chem. Front., 2015,2, 1318-1321
Article type
Research Article
Author version available

Palladium-catalyzed alkylation of unactivated C(sp3)–H bonds with primary alkyl iodides at room temperature: facile synthesis of β-alkyl α-amino acids

B. Wang, X. Wu, R. Jiao, S.-Y. Zhang, W. A. Nack, G. He and G. Chen, Org. Chem. Front., 2015, 2, 1318
DOI: 10.1039/C5QO00112A

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