Chiral Heterospirocyclic 2H??Azirin??3??amines as Synthons for 3??Amino??2, 3, 4, 5??tetrahydrofuran??3??carboxylic Acid and Their Use in Peptide Synthesis

S Stamm, A Linden, H Heimgartner

Index: Stamm, Simon; Linden, Anthony; Heimgartner, Heinz Helvetica Chimica Acta, 2003 , vol. 86, # 5 p. 1371 - 1396

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Citation Number: 19

Abstract

Abstract The heterospirocyclic N-methyl-N-phenyl-5-oxa-1-azaspiro [2.4] hept-1-e n-2-amine (6) and N-(5-oxa-1-azaspiro [2.4] hept-1-en-2-yl)-(S)-proline methyl ester (7) were synthesized from the corresponding heterocyclic thiocarboxamides 12 and 10, respectively, by consecutive treatment with COCl 2, 1, 4-diazabicyclo [2.2. 2] octane, and NaN 3 (Schemes 1 and 2). The reaction of these 2H-azirin-3-amines with thiobenzoic and ...