Pd(II)/Norbornene-Catalyzed Meta-C–H Alkylation of Nosyl-Protected Phenylalanines

A Pd/norbornene-catalyzed direct meta-alkylation of nosyl-protected phenylalanine derivatives with alkyl iodides is reported in moderate to good yields. The use of diisopropyl bicyclo[2.2.1]­hept-5-ene-2,3-dicarboxylate is identified as a more suitable transient mediator. A simple pyridine ligand is...

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Published inJournal of organic chemistry Vol. 83; no. 21; pp. 13211 - 13216
Main Authors Liu, Jieyu, Ding, Qiuping, Fang, Wenjun, Wu, Wanhui, Zhang, Yuanguang, Peng, Yiyuan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.11.2018
Amer Chemical Soc
Subjects
alkylation
chemical structure
Chemistry
Chemistry, Organic
ligands
organic chemistry
organoiodine compounds
phenylalanine
Physical Sciences
pyridines
Science & Technology
CATALYSIS
AMINATION
PEPTIDES
ANALOGS
ARYLATION
BONDS
INDOLINES
DERIVATIVES
ALKENYLATION
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Summary:A Pd/norbornene-catalyzed direct meta-alkylation of nosyl-protected phenylalanine derivatives with alkyl iodides is reported in moderate to good yields. The use of diisopropyl bicyclo[2.2.1]­hept-5-ene-2,3-dicarboxylate is identified as a more suitable transient mediator. A simple pyridine ligand is also essential for this reaction to proceed. No racemization was observed in this meta-methylation reaction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.8b01933