手性高价碘试剂诱导的不对称去芳构化反应研究进展

doi:10.6023/cjoc202304008

摘要/Abstract

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.

关键词: 手性高价碘, 去芳构化反应, 不对称合成, 天然产物

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.

Key words: chiral hypervalent iodine, dearomatization, asymmetric synthesis, natural product

引用此文

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.

Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.

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图/表 30

图式1. 手性碘化物5a的合成

Scheme 1. Synthesis of chiral iodine compound 5a

图式2. 手性碘化物13的合成

Scheme 2. Synthesis of chiral iodine compound 13

图式3. 手性碘化物34的合成

Scheme 3. Synthesis of chiral iodine compound 34

图式4. 手性碘化物47的合成

Scheme 4. Synthesis of chiral iodine compound 47

图式5. 手性高价碘试剂诱导的萘酚8a不对称去芳构化反应机理

Scheme 5. Mechanisms for asymmetric dearomatization of naphthol 8a induced by chiral hypervalent iodine reagents

图式6. 手性高价碘化物65的合成

Scheme 6. Synthesis of chiral hypervalent iodine compound 65

图式7. 手性高价碘化合物65诱导的酚22的不对称去芳构化/[4+2]环加成反应

Scheme7 Asymm. etric dearomatization/[4+2] cycloaddition of phenols 22 induced by chiral hypervalent iodine compound 65 Asymmetric dearomatization/[4+2] cycloaddition of phenols 22 induced by chiral hypervalent iodine compound 65

图式8. 手性碘化物70的合成

Scheme 8. Synthesis of chiral iodine compound 70

图式9. 手性碘化物70诱导的萘酚8a去芳构化反应的可能中间体

Scheme 9. Possible intermediates of dearomatization of 8a induced by chiral iodine compound 70

图式10. 手性碘化物77的合成

Scheme 10. Synthesis of chiral iodine compound 77

图式11. 手性碘化物80的合成

Scheme 11. Synthesis of chiral iodine compound 80

图式12. 手性高价碘化合物86的合成

Scheme 12. Synthesis of chiral hypervalent iodine compounds 86

图式13. 手性高价碘化合物92的合成

Scheme 13. Synthesis of chiral hypervalent iodine compound 92

图式14. 手性高价碘96诱导酚的氧化去芳构化反应机理

Scheme 14. Mechanism of dearomatization of phenols mediated by chiral hypervalent iodine compound 96

图式15. 手性碘化物105的合成

Scheme 15. Synthesis of chiral iodine compound 105

图式16. 手性高价碘化物109的合成

Scheme 16. Synthesis of chiral hypervalent iodine compound 109

图式17. 手性碘化物112的合成

Scheme 17. Synthesis of chiral iodine compound 112

图式18. 手性碘化物112诱导萘酚8的氧化去芳构化反应机理

Scheme18. Mechanism of dearomatization of naphthols 8 mediated by chiral iodine compound 112

图式19. 手性碘化物108诱导萘酚8a的氧化去芳构化反应机理

Scheme19. Mechanism of dearomatization of naphthol 8a mediated by chiral iodine compound 108

图式20. 手性高价碘化物125的合成

Scheme 20. Synthesis of chiral hypervalent iodine compound 125

图式21. 手性碘化物129的合成

Scheme 21. Synthesis of chiral iodine compound 129

图式22. 手性碘化物132的合成

Scheme 22. Synthesis of chiral iodine compound 132

图式23. 手性碘化物135和137的合成

Scheme 23. Synthesis of chiral iodine compounds 135 and 137

图式24. 手性碘化物145的合成

Scheme 24. Synthesis of chiral iodine compound 145

图式25. 手性碘化物151a的合成

Scheme 25. Synthesis of chiral iodine compound 151a

图式26. 手性碘化物157的合成

Scheme 26. Synthesis of chiral iodine compound 157

图式27. 手性高价碘化物162的合成

Scheme 27. Synthesis of chiral hypervalent iodine compound 162

图式28. 手性高价碘化物167的合成

Scheme 28. Synthesis of chiral hypervalent iodine compound 167

图式29. Scyphostain类似物173和176的合成

Scheme 29. Synthesis of scyphostain analogues 173 and 176

图式30. (–)-Maldoxin的全合成

Scheme 30. Total synthesis of (–)-maldoxin

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