Palladium-catalyzed alkylation of unactivated C(sp3)-H bonds with primary alkyl iodides at room temperature: Facile synthesis of β-alkyl α-amino acids

B. Wang, X. Wu, R. Jiao, S. Y. Zhang, W. A. Nack, G. He, G. Chen

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

An efficient protocol for the synthesis of β-alkyl α-amino acids via palladium-catalyzed β-C(sp3)-H alkylation of aminoquinoline-coupled phthaloyl alanine is developed. The new TFA-promoted reaction conditions provide excellent C-H alkylation reactivity with alkyl iodides bearing moderately electronwithdrawing groups at room temperature. A range of β-alkyl α-amino acid products, including some difficult to access by other means, can be quickly prepared from readily available primary alkyl iodides and alanine precursors.

Original languageEnglish (US)
Pages (from-to)1318-1321
Number of pages4
JournalOrganic Chemistry Frontiers
Volume2
Issue number10
DOIs
StatePublished - Oct 1 2015

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this