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

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...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 17; pp. 3870 - 3873
Main Authors Meyer, Falco-Magnus, Liras, Spiros, Guzman-Perez, Angel, Perreault, Christian, Bian, Jianwei, James, Keith
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.09.2010
Amer Chemical Soc
Subjects
Amino Acids, Aromatic - chemical synthesis
Amino Acids, Aromatic - chemistry
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Iridium - chemistry
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
BIS(PINACOLATO)DIBORON
IMINES
COUPLING REACTION
ARENES
ASYMMETRIC STRECKER REACTION
PHASE-TRANSFER CATALYSIS
INERT SOLVENT
DYNAMIC KINETIC RESOLUTION
ROOM-TEMPERATURE REACTIONS
BORYLATION
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol1015674