Letter

Functionalization of Aromatic Amino Acids via Direct C−H Activation: Generation of Versatile Building Blocks for Accessing Novel Peptide Space

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, and CVMED Chemistry, Pfizer Inc., 445 Eastern Point Road, Groton, Connecticut 06340
Org. Lett., 2010, 12 (17), pp 3870–3873
DOI: 10.1021/ol1015674
Publication Date (Web): August 9, 2010
Copyright © 2010 American Chemical Society
kjames@scripps.edu, †

The Scripps Research Institute.

, ‡

Pfizer Inc.

Abstract

Abstract Image

Functionalized α-amino acid building blocks have been prepared in good yield with high regiocontrol and preservation of stereochemistry via iridium-catalyzed borylation of suitably protected aromatic α-amino acid derivatives. The utility of these systems in peptide couplings and Suzuki reactions has been demonstrated.

Experimental procedures and full spectroscopic data for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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Article Views: 2,485 Times
Received 7 July 2010
Published online 9 August 2010
Published in print 3 September 2010
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