Unusual rearrangement of spiro β-lactams to 1,4-diazabicyclo[4,4,0]decanes and 1,4-diazabicyclo[4,3,0]nonanes. Synthesis of conformationally restricted σ-receptor ligands

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• 作者：Mací ; as ; Alberto ; Alonso ; Eduardo ; del Pozo ; Carlos ; Gonzá ; lez ; Javier
• 关键词：Rearrangement ; Spiro β ; -lactams ; 1 ; 4-Diazabicyclo[4 ; 4 ; 0]decanes ; 1 ; 4-Diazabicyclo[4 ; 3 ; 0]nonanes ; Retro-Mannich reactions ; σ ; -Receptors
• 刊名：Tetrahedron Letters
• 出版年：2004
• 出版时间：June 7, 2004
• 年：2004
• 卷：45
• 期：24
• 页码：4657-4660
• 全文大小：271 K

文摘

Synthesis of 1,4-diazabicyclo[4,4,0]decanes and 1,4-diazabicyclo[4,3,0]nonanes was achieved by using 4-formyl spiro β-lactams as easily available starting materials. Furthermore, the application of this protocol to the preparation of conformationally restricted σ-receptor ligands was also performed. Theoretical calculations were carried out on a model reaction, in order to give some understanding of the reaction mechanism.