Showa Pharmaceutical University.
Chem Pharm Bull (Tokyo). 2024;72(8):731-746. doi: 10.1248/cpb.c24-00343.
Nitrones are widely used as 1,3-dipoles in organic synthesis, but control of their reactions is not always easy. This review outlines our efforts to make the reactions of nitrones more predictable and easier to use. These efforts can be categorized into (1) 1,3-nucleophilic addition reaction of ketene silyl acetals to nitrones, (2) geometry-controlled cycloaddition of C-alkoxycarbonyl nitrones, (3) stereo-controlled cycloaddition using double asymmetric induction, and (4) generation of nitrones by N-selective modification of oximes.
硝酮广泛用作有机合成中的 1,3-偶极子，但对其反应的控制并不总是容易的。本综述概述了我们努力使硝酮的反应更具可预测性和更易于使用。这些努力可以分为（1）烯酮硅基缩醛对硝酮的 1,3-亲核加成反应，（2）C-烷氧基羰基硝酮的几何控制环加成，（3）使用双重不对称诱导的立体控制环加成，和（4）通过肟的 N-选择性修饰生成硝酮。
