手性高价碘试剂诱导的不对称去芳构化反应研究进展
收稿日期: 2023-04-06
修回日期: 2023-05-27
网络出版日期: 2023-06-26
基金资助
甘肃省高等学校青年博士基金(2022QB-206)
Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents
Received date: 2023-04-06
Revised date: 2023-05-27
Online published: 2023-06-26
Supported by
the Young Doctor’s Projects of Universities in Gansu Province(2022QB-206)
不对称去芳构化反应可以将平面、非手性的芳烃类化合物转变为具有三维结构的手性化合物, 因此该类反应成为制备手性分子、药物和天然产物的一种重要策略. 手性高价碘试剂由于具有反应条件温和、环境友好及对映选择高等优点, 被广泛用于不对称氧化反应中. 就近20年来手性高价碘试剂诱导的去芳构化反应进行综述, 根据手性骨架的不同, 分为手性乳酸酯衍生物、联萘、酒石酸、螺环、杂环, 及其他骨架如糖、[2,2]-对环芳烃和三蝶烯等, 从合成的方法、诱导的不对称反应及代表性的实例详细介绍了每类手性试剂. 此外, 还总结了手性高价碘试剂诱导的去芳构化反应在天然产物合成中的应用.
张怀远 , 许诺 , 唐蓉萍 , 石星丽 . 手性高价碘试剂诱导的不对称去芳构化反应研究进展[J]. 有机化学, 2023 , 43(11) : 3784 -3805 . DOI: 10.6023/cjoc202304008
Asymmetric dearomatization reactions can transform planar, achiral aromatic compounds into chiral compounds with three-dimensional structures, making them as an important strategy for the preparation of chiral molecules, drugs, and natural products. Chiral hypervalent iodine reagents are widely used in asymmetric oxidation due to their advantages of mild reaction conditions, environment friendliness and excellent enantioselectivity. The dearomatization reactions induced by chiral hypervalent iodine reagents in the past 20 years are summarized. According to the different chiral skeletons, they are divided into chiral lactate derivatives, binaphthyl, tartrate, spiro rings, heterocycles, and other skeletons such as carbohydrate, [2.2]-para-cyclophane, triptycenes, etc. Each type of these chiral reagents is introduced in detail from the aspect of preparation, asymmetric reactions, and typical examples. In addition, the application of dearomatization reactions induced by chiral hypervalent iodine reagents in the total synthesis of natural products is also summarized.
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