Synthesis of 3-Aryl-1-aminopropane Derivatives: Lithiation-Borylation-Ring-Opening of Azetidinium Ions
Synthesis of 3-Aryl-1-aminopropane Derivatives: Lithiation-Borylation-Ring-Opening of Azetidinium Ions
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DOI：
10.1055/s-0035-1562447
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发表时间：
2016-10-01
影响因子：
2.6
通讯作者：
Aggarwal, Varinder K.
中科院分区：
文献类型：
--
作者：
Casoni, Giorgia;Myers, Eddie L.;Aggarwal, Varinder K.
原位生成的2-苯基叠氮基醚与硼酯反应生成无环-二甲胺叔硼酯。这种转变被认为涉及到一个两性离子硼酸盐的形成，随后经历开环1,2迁移，这是由环应变的缓解促进。由于初始形成的酰基的构型不稳定，它似乎与开链碳烷形式处于平衡状态，因此该反应不具有立体特异性。碳- b键。-二甲氨基叔硼酯可以转化为多种官能团（C-OH， c -乙烯基，C-H, C-BF3），从而使3-芳基-1-氨基丙烷具有多种选择，这是药物分子中的特权基序。
In situ generated 2-phenyl-azetidinium ylides react with boronic esters to form acyclic gamma-dimethylamino tertiary boronic esters. The transformation is believed to involve the formation of a zwitterionic boronate, which subsequently undergoes ring-opening 1,2-migration, which is promoted by the relief of ring strain. Owing to the configurational instability of the initially formed ylides, which appear to be in equilibrium with the open-chain carbene form, the reaction is not stereospecific. The C-B bond of the.-dimethylamino tertiary boronic esters can be transformed into a variety of functional groups (C-OH, C-vinyl, C-H, C-BF3), thus giving a diverse selection of 3-aryl-1-aminopropanes, which represent a privileged motif among drug molecules.