Tetrahedron

Synthesis and reactivity of methyl γ-azido butyrates and ethyl σ-azido valerates and of the corresponding acid chlorides as useful reagents for the aminoalkylation

N Khoukhi, M Vaultier, R Carrie

Index: Khoukhi, N.; Vaultier, M.; Carrie, R. Tetrahedron, 1987 , vol. 43, # 8 p. 1811 - 1822

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Citation Number: 76

Abstract

The azidoesters 13 and 14 and the corresponding acid chlorides 22 and 23 are shown to be interesting reagents for the nucleophilic and electrophilic aminoalkylation. α-substituted methyl γ-azidobutyrates 13 and ethyl σ-azido valerates 14 are easily accessible by alkylation of the lithium enolates of the parent compounds 13a and 14a respectively. Their chemoselective reduction leads to 3-substituted lactams 18 and 19. The acid chlorides 22 ...