CSIRO Publishing

An international journal for chemical science

Shopping Cart: ( empty )

RESEARCH FRONT

Previous Next Contents Vol 60(11)

Organoboron Reagents in the Preparation of Functionalized α-Amino Acids

Peter F. Kaiser ^A , Quentin I. Churches ^A and Craig A. Hutton ^A ^B

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne VIC 3010, Australia.

^B Corresponding author. Email: chutton@unimelb.edu.au

Peter Kaiser studied chemistry at the Technical University of Munich, and received his B.Sc. in 2003 and his M.Sc. in 2004. He is currently doing a Ph.D. on new methods for amino acid and peptide synthesis under the supervision of Dr Craig Hutton at The University of Melbourne.

Quentin Churches studied chemistry at Royal Melbourne Institute of Technology and later The University of Melbourne where he received his B.Sc.(Hons) in 2005. Quentin is currently working towards his Ph.D. at The University of Melbourne under the guidance of Dr Craig Hutton and his current research interests are in the development of new methodology for synthesis of unusual amino acids and the use of boronic acids in synthesis.

Craig Hutton obtained his undergraduate and Ph.D. degrees from the University of Adelaide before completing postdoctoral studies at the University of California, Berkeley and The University of Melbourne (Australian Postdoctoral Research Fellow). He was then appointed to the School of Chemistry at The University of Sydney, before returning to The University of Melbourne in 2003. His research interests include novel methods for the synthesis of unusual amino acids and cyclic peptide natural products, and the design and synthesis of inhibitors of enzymes in the lysine biosynthetic pathway.

Australian Journal of Chemistry 60(11) 799-810 https://doi.org/10.1071/CH07103
Submitted: 5 April 2007 Accepted: 4 July 2007 Published: 1 November 2007

Abstract

Over the past decade, major advances in the preparation and utilization of organoboron reagents have been applied to virtually all areas of organic synthesis. The present review collates recent examples of the use of organoboron reagents in the synthesis of α-amino acids and their derivatives. Aryl- and alkenylboronic acids have been used in the asymmetric synthesis of α-amino acids through conjugate addition to unsaturated amino acids and the Petasis three-component coupling reaction. Additionally, α-amino acid derivatives with organoboron functionality on the side-chain have been prepared and used in metal-catalyzed cross-coupling reactions to prepare cross-linked amino acids and complex cyclic peptide natural products.

Acknowledgments

CAH thanks the Australian Research Council for funding.

References

[1] Boronic Acids – Preparation, Applications in Organic Synthesis and Medicine (Ed. Hall D. G.) 2005 (Wiley-VCH: Weinheim).

[2] W. Yang, X. Gao, B. Wang, Med. Res. Rev. 2003, 23, 346.
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |

        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |
        | Crossref | GoogleScholarGoogle Scholar |