分子内氢键促进的大环合成: 动力学和热力学控制途径

doi:10.6023/cjoc201207034

摘要/Abstract

氢键诱导的线性芳酰胺寡聚体骨架可以采取折叠、螺旋、直线或“之”字型构象. 这一结构预组织特征可以被应用于促进大环的合成. 在芳酰胺骨架的两端引入适当反应基团, 骨架的预组装构象可以诱导它们形成不同的空间取向和距离. 当成环反应涉及到不可逆共价键、碳-金属键或配位键的形成时, 前体的结构预组织构象可以促进目标大环形成的产率. 当成环反应涉及亚胺及腙等可逆共价键时, 在反应达到热力学平衡后, 可以高产率或定量地形成大环.

关键词: 氢键, 大环, 芳香酰胺, 亚胺, 动力学控制反应, 热力学控制反应

Hydrogen bonding-induced aromatic amide oligomers may adopt folded, helical, extended or zigzag conformations. This feature of structural preorganization can be utilized to promote the formation of macrocycles. When reactive groups are introduced at the ends of the aromatic amide backbones, the preorganization of the backbones may induce them to adopt discrete required spatial orientations. When macrocyclization concerns the formation of irreversible covalent, carbon-metal and coordination bonds, preorganization may facilitate the formation of specifically designed macrocycles. When macrocyclization involves the formation of reversible covalent bonds such as imine and hydrazone, rationally designed macrocycles may be produced in high or even quantitative yields after the reactions achieve equilibrium and are controlled thermodynamically.

Key words: hydrogen bonding, macrocycle, aromatic amide, imine, dynamically controlled reaction, thermodynamically controlled reaction

引用此文

张丹维, 黎占亭. 分子内氢键促进的大环合成: 动力学和热力学控制途径[J]. 有机化学, 2012, 32(11): 2009-2017.

Zhang Danwei, Li Zhanting. Intramolecular Hydrogen Bonding-Promoted Formation of Macrocycles: Dynamical and Thermodynamic Control Approaches[J]. Chin. J. Org. Chem., 2012, 32(11): 2009-2017.

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