Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis

Liu, S.; Yang, Y.; Liu, X.; Ferdousi, F.K.; Batsanov, A.S.; Whiting, A.

doi:10.1002/ejoc.201300560

Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis

Liu, S.; Yang, Y.; Liu, X.; Ferdousi, F.K.; Batsanov, A.S.; Whiting, A.

Authors

S. Liu

Y. Yang

X. Liu

F.K. Ferdousi

A.S. Batsanov

Professor Andrew Whiting andy.whiting@durham.ac.uk
Emeritus Professor

Abstract

The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65–68 °C generally avoiding racemization. 3,4,5-Trifluorophenylboronic and o-nitrophenylboronic acids were found to be the best catalysts, though for slower dipeptide formations, high catalyst loadings were required and an interesting synergistic catalytic effect between two arylboronic acids was discovered.

Citation

Liu, S., Yang, Y., Liu, X., Ferdousi, F., Batsanov, A., & Whiting, A. (2013). Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis. European Journal of Organic Chemistry, 2013(25), 5692-5700. https://doi.org/10.1002/ejoc.201300560

Journal Article Type	Article
Publication Date	Sep 1, 2013
Deposit Date	Nov 22, 2013
Publicly Available Date	May 22, 2014
Journal	European Journal of Organic Chemistry
Print ISSN	1434-193X
Electronic ISSN	1099-0690
Publisher	Wiley
Peer Reviewed	Peer Reviewed
Volume	2013
Issue	25
Pages	5692-5700
DOI	https://doi.org/10.1002/ejoc.201300560
Keywords	Amides, Amino acids, Peptides, Organocatalysis, Synethic methods.

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Copyright Statement
This is the peer reviewed version of the following article: Liu, S., Yang, Y., Liu, X., Ferdousi, F. K., Batsanov, A. S. and Whiting, A. (2013), Direct Amidation of Amino Acid Derivatives Catalyzed by Arylboronic Acids: Applications in Dipeptide Synthesis. European Journal of Organic Chemistry, 2013 (25): 5692-5700, which has been published in final form at http://dx.doi.org/10.1002/ejoc.201300560. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for self-archiving.