Palladium-catalyzed trifluoroacetate-promoted mono-arylation of the β-methyl group of alanine at room temperature: Synthesis of β-arylated α-amino acids through sequential C-H functionalization

Bo Wang, William A. Nack, Gang He, Shu Yu Zhang, Gong Chen

Research output: Contribution to journalArticlepeer-review

95 Scopus citations

Abstract

We report a highly efficient and practical protocol for palladium-catalyzed N-quinolylcarboxamide (AQ)-directed arylation of the unactivated β-C(sp3)-H bonds of alanine with aryl iodides at room temperature. For the first time, a broad range of easily accessible aryl iodides can be installed onto the β-methyl group of AQ-coupled phthaloyl alanine mono-selectively, providing both natural and unnatural aromatic α-amino acids. Access to these mono-arylated compounds enables subsequent AQ-directed diastereoselective C-H functionalization, allowing the preparation of various β-disubstituted aromatic α-amino acids in a programmable manner.

Original languageEnglish (US)
Pages (from-to)3952-3957
Number of pages6
JournalChemical Science
Volume5
Issue number10
DOIs
StatePublished - Oct 2014

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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