4-Vinylproline

• DOI: 10.1021/acs.joc.8b02177
• Publication Date: 2018-09-24T14:09:37Z
• Authors: Ramakotaiah Mulam...; N. D. Prasad Atmuri; William D. Lubell
• Keywords: 01 natural sciences; 0104 chemical sciences

Enantiomerically pure 4-vinylproline (Vyp) was synthesized by a five-step approach from N-(Boc)iodo-alanine (2) featuring copper-catalyzed SN2' substitution of the corresponding zincate onto ( Z)-1,4-dichlorobut-2-ene to prepare methyl 2- N-(Boc)amino-4-(chloromethyl)hexenoate (3). Intra- and intermolecular displacement of the chloride provided respectively Vyp and methyl 2- N-(Boc)amino-4-(azidomethyl)hexenoate (7) suitable for the synthesis of constrained peptide analogs.