Details

Autor(en) / Beteiligte

• Zhang, Shu-Yu
• Li, Qiong
• He, Gang
• Nack, William A
• Chen, Gong

Titel

Stereoselective Synthesis of β‑Alkylated α‑Amino Acids via Palladium-Catalyzed Alkylation of Unactivated Methylene C(sp3)–H Bonds with Primary Alkyl Halides

Ist Teil von

• Journal of the American Chemical Society, 2013-08, Vol.135 (32), p.12135-12141

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2013

Quelle

MEDLINE

Beschreibungen/Notizen

• We report a new set of reactions based on the Pd-catalyzed alkylation of methylene C(sp3)–H bonds of aliphatic quinolyl carboxamides with α-haloacetate and methyl iodide and applications in the stereoselective synthesis of various β-alkylated α-amino acids. These reactions represent the first generally applicable method for the catalytic alkylation of unconstrained and unactivated methylene C–H bonds with high synthetic relevance. When applied with simple isotope-enriched reagents, they also provide a convenient and powerful means to site-selectively incorporate isotopes into the carbon scaffolds of amino acid compounds.