Flexible, Phase-Transfer Catalyzed Approaches to 4‑Substituted Prolines

• Published in: Organic letters Vol. 16; no. 18; pp. 4778 - 4781
• Main Authors: Johnston, Heather J, McWhinnie, Fergus S, Landi, Felicetta, Hulme, Alison N
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 19.09.2014; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Organic; Glycine - chemistry; Hydrogenation; Molecular Structure; Oligopeptides - pharmacology; Physical Sciences; Proline - analogs & derivatives; Proline - chemical synthesis; Proline - chemistry; Schiff Bases; Science & Technology; Stereoisomerism; ALPHA-AMINO-ACIDS; PEPTIDES; ENANTIOSELECTIVE SYNTHESIS; METATHESIS

A range of 4-substituted prolines can be rapidly synthesized from a protected glycine Schiff base in only four steps and in 27–55% overall yield. Phase transfer catalysis allows direct access to both enantiomeric series, and the relative stereochemistry at the 4-position is readily controlled (>1...