Functionalization of aromatic amino acids via direct C-H activation: generation of versatile building blocks for accessing novel peptide space

Falco-Magnus Meyer; Spiros Liras; Angel Guzman-Perez; Christian Perreault; Jianwei Bian; Keith James

doi:10.1021/ol1015674

Functionalization of aromatic amino acids via direct C-H activation: generation of versatile building blocks for accessing novel peptide space

Org Lett. 2010 Sep 3;12(17):3870-3. doi: 10.1021/ol1015674.

Authors

Falco-Magnus Meyer¹, Spiros Liras, Angel Guzman-Perez, Christian Perreault, Jianwei Bian, Keith James

Affiliation

¹ Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

PMID: 20695449
DOI: 10.1021/ol1015674

Abstract

Functionalized alpha-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 alpha-amino acid derivatives. The utility of these systems in peptide couplings and Suzuki reactions has been demonstrated.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids, Aromatic / chemical synthesis*
Amino Acids, Aromatic / chemistry
Catalysis
Combinatorial Chemistry Techniques
Iridium / chemistry
Molecular Structure
Peptides / chemical synthesis*
Peptides / chemistry
Stereoisomerism

Substances

Amino Acids, Aromatic
Peptides
Iridium