Enantioselective synthesis of arylglycine derivatives by direct C-H oxidative cross-coupling

A new method for the synthesis of chiral alpha-amino acid derivatives by enantioselective C-H arylation of N-aryl glycine esters with aryl boric acids in the presence of a chiral Pd(II)-catalyst has been developed. This work successfully integrates the direct C-H oxidation with asymmetric arylation...

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Published inChemical communications (Cambridge, England) Vol. 51; no. 5; pp. 832 - 835
Main Authors Wei, Xiao-Hong, Wang, Gang-Wei, Yang, Shang-Dong
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 18.01.2015
Subjects
Aromatic compounds
Asymmetry
Boric acids
Carbon - chemistry
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Multidisciplinary
Cross coupling
Derivatives
Esters
Glycine
Glycine - analogs & derivatives
Glycine - chemical synthesis
Glycine - chemistry
Hydrogen - chemistry
Oxidation-Reduction
Physical Sciences
Science & Technology
Stereoisomerism
Substrate Specificity
Synthesis
PHOSPHORUS LIGANDS
ALPHA-AMINO
ASYMMETRIC-SYNTHESIS
MANNICH-TYPE REACTION
TERTIARY-AMINES
AMINO-ACID DERIVATIVES
PHASE-TRANSFER CATALYSIS
BOND FUNCTIONALIZATION
STEREOSELECTIVE-SYNTHESIS
ARYLBORONIC ACIDS
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Summary:A new method for the synthesis of chiral alpha-amino acid derivatives by enantioselective C-H arylation of N-aryl glycine esters with aryl boric acids in the presence of a chiral Pd(II)-catalyst has been developed. This work successfully integrates the direct C-H oxidation with asymmetric arylation and exhibits excellent enantioselectivity.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc07361d