2. Academic Validation
  3. Synthesis of Fmoc-Protected Arylphenylalanines (Bip Derivatives) via Nonaqueous Suzuki-Miyaura Cross-Coupling Reactions

Synthesis of Fmoc-Protected Arylphenylalanines (Bip Derivatives) via Nonaqueous Suzuki-Miyaura Cross-Coupling Reactions

  • J Org Chem. 2016 Oct 7;81(19):9499-9506. doi: 10.1021/acs.joc.6b01965.
Jennifer X Qiao 1,  Kenneth J Fraunhoffer 1,  Yi Hsiao 1,  Yi-Xin Li 1,  Chunlei Wang 1,  Tammy C Wang 1,  Michael A Poss 1
Affiliations

Affiliation

  • 1 Discovery Chemistry, ‡Chemical and Synthetic Development, and §Pharmaceutical Candidate Optimization, Research and Development, Bristol-Myers Squibb Company , P.O. Box 4000, Princeton, New Jersey 08543-4000, United States.
PMID: 27615449 DOI: 10.1021/acs.joc.6b01965
Abstract

A one-step synthesis of Fmoc-protected aryl/heteroaryl-substituted phenylalanines (Bip derivatives) using the nonaqueous palladium-catalyzed Suzuki-Miyaura cross-coupling (SMC) reaction of Fmoc-protected bromo- or iodophenylalanines is reported. This protocol allows for the direct formation of a variety of unnatural biaryl-containing Amino acids in good to excellent yield, which can be readily used in subsequent Fmoc solid-phase peptide synthesis. The synthetic utility of this method is also demonstrated by the SMC reaction of bromophenylalanine-containing tripeptides.

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