Tetrahedron

Isopropenyl chlorocarbonate (IPCC) 1 in amino acid and peptide chemistry: esterification of N-protected amino acids; application to the synthesis of the depsipeptide …

C Zeggaf, J Poncet, P Jouin, MN Dufour, B Castro

文献索引：Zeggaf, Choukri; Poncet, Joel; Jouin, Patrick; Dufour, Marie-Noelle; Castro, Bertrand Tetrahedron, 1989 , vol. 45, # 16 p. 5039 - 5050

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被引用次数: 33

摘要

Esterification of N-protected α-amino acids was achieved via isopropenyl chlorocarbonate (IPCC) activation. In situ alcoholysis of the unstable mixed anhydride intermediate was catalyzed by 4-(dimethylamino) pyridine (DMAP). Competing isopropenyl ester formation was negligible when using methylene chloride as the solvent. A variety of esters from primary and secondary alcohols were obtained with good yields (60 to 96%), and even ...