氮杂环丁烷类化合物是一类重要的饱和四元含氮杂环化合物，不仅是有机合成中的重要原料、中间体及手性助剂或催化剂，也是氨基酸、生物碱及其天然和合成生物活性或药物活性化合物等分子结构中的重要活性单元。因此，发展氮杂环丁烷结构的合成方法非常重要。本文综述了氮杂环丁烷类化合物合成的发展，着重综述了近十年来该类化合物合成方法的进展，主要包括形成C—N键成环、形成C—C键成环、胺催化的亚胺和丙二烯甲酸酯环加成、亚胺和烯烃的光环加成、缩环扩环重排和氮杂环丁-2-酮（β-内酰胺）还原等方法构建氮杂环丁烷结构的新成果。
Azetidines, as an important class of saturated four-membered azaheterocycles, are not only important raw materials, intermediates, chiral auxiliaries and catalysts in organic synthesis, but also crucial active structural units of amino acids, alkaloids, natural and synthetic biological and medicinal active compounds. Thus, it is critical to develop methods for constructing azetidine structural motifs. The review introduces the development of the synthesis of azetidines and mainly focuses on advances of the synthesis of azetidines during recent 10 years. Furthermore, it demonstrates the new achievements in the synthesis of azetidines mainly including cyclizations by the C-N bond formation and by the C-C bond formation, amine-catalyzed cycloaddition of allenoates and imines, photocycloadditions of imines and alkenes, ring contraction and expansion rearrangements, and reduction of azetidin-2-ones(β-lactams).
Contents
1 Introduction
2 Cyclizations by the C-N bond formation
2.1 Nucleophilic substitution reactions
2.2 Reductive cyclizations of β-haloalkylimines
2.3 Cyclizations of allylic and homoallylic amines
2.4 Opening of epoxides with amines
2.5 Opening of aziridines
2.6 Pd-Catalyzed cyclizations
3 Cyclizations by the C-C bond formation
3.1 Nucleophilic displacements
3.2 Cyclizations involving Michael additions
4 Cycloadditions
4.1 Amine-catalyzed cycloadditions of allenoates and imines
4.2[2+2]Photocycloadditions of imines and alkenes
5 Ring contraction and expansion rearrangements
5.1 Ring contractions of five-membered heterocycles
5.2 Ring expansions of three-membered heterocycles
6 Reduction of azetidin-2-ones
7 Conclusion
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