Palladium-catalyzed stereoretentive olefination of unactivated C(sp3)-H bonds with vinyl iodides at room temperature: Synthesis of β-vinyl α-amino acids

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

Research output: Contribution to journalArticlepeer-review

68 Scopus citations

Abstract

A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp3)-H bonds of phthaloyl alanine with a broad range of vinyl iodides at room temperature. This reaction represents the first example of the stereoretentive installation of multisubstituted terminal and internal olefins onto unactivated C(sp3)-H bonds. These methods enable access to a wide range of challenging β-vinyl α-amino acid products in a streamlined and controllable fashion, beginning from simple precursors.

Original languageEnglish (US)
Pages (from-to)6260-6263
Number of pages4
JournalOrganic Letters
Volume16
Issue number23
DOIs
StatePublished - Dec 5 2014

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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