Intramolecular Pyridinium Oxide Cycloadditions: Systematic Study of Substitution, Diastereoselectivity, and Regioselectivity
Intramolecular Pyridinium Oxide Cycloadditions: Systematic Study of Substitution, Diastereoselectivity, and Regioselectivity
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分子内氧化吡啶环加成：取代、非对映选择性和区域选择性的系统研究
DOI：
10.1002/chem.202100115
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发表时间：
2021
期刊：
影响因子：
--
通讯作者：
Beaudry, Christopher M.
中科院分区：
文献类型：
--
作者：
Lu, Yi;Dey, Patrick N.;Beaudry, Christopher M.
分子内氧化吡啶环加成形成复杂的多环含氮结构。首次系统地研究了吡啶氧化物环加成反应的非对映选择性和区域选择性。观察到可预测的高水平的非对映选择性和区域选择性，这可归因于产物中的空间（顺戊烷）和扭转应变的最小化。该反应在反应条件下是可逆的，并且其相对于偶极亲电体几何形状是立体特异性的。
Intramolecular pyridinium oxide cycloadditions form complex polycyclic nitrogenous architectures. The diastereoselectivity and regioselectivity of pyridinium oxide cycloadditions was systematically investigated for the first time using complex substrates. Predictably high levels of diastereoselectivity and regioselectivity are observed, which can be attributed to minimization of steric (syn‐pentane) and torsional strain in the products. The reaction is reversible under the reaction conditions, and it is stereospecific with respect to the dipolarophile geometry.