2-吡喃酮的催化不对称Diels-Alder反应研究进展

doi:10.6023/cjoc202109025

摘要/Abstract

2-吡喃酮是一种含有共轭二烯的杂环化合物, 它可以作为一种特殊的双烯体参与Diels-Alder反应. 经过几十年的发展, 2-吡喃酮的Diels-Alder反应在复杂天然产物的合成中得到了广泛地应用. 近年来, 2-吡喃酮的催化不对称Diels-Alder反应也引起了合成化学家的关注. 对2-吡喃酮参与的不对称正电子需求和反电子需求的Diels-Alder反应的发展, 以及它们在天然产物全合成中的应用进行了总结.

关键词: 2-吡喃酮, Diels-Alder反应, 不对称催化, 天然产物全合成

2-Pyrone is a type of heterocycles with a conjugated diene motif. It can react as a privileged diene in Diels-Alder reactions. In the past several decades, 2-pyrone-based Diels-Alder reactions have been widely used in the total synthesis of complex natural products. Therefore, the catalytic asymmetric Diels-Alder reactions of 2-pyrones have attracted increasing attention from the synthetic community in recent years. The research progress of catalytic asymmetric normal-electron-demand Diels-Alder reactions and inverse-electron-demand Diels-Alder reactions, and their applications in total synthesis of natural products are summarized.

Key words: 2-pyrone, Diels-Alder reactions, asymmetric catalysis, total synthesis of natural products

引用此文

徐萌萌, 蔡泉. 2-吡喃酮的催化不对称Diels-Alder反应研究进展[J]. 有机化学, 2022, 42(3): 698-713.

Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones[J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.

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图/表 22

图式1. 首例2-吡喃酮的Diels-Alder反应

Scheme 1. The first example of Diels-Alder reaction of 2-pyrone

图式2. 2-吡喃酮的Diels-Alder反应

Scheme 2. Diels-Alder reaction of 2-pyrones

图式3. 2-吡喃酮的正电子需求的Diels-Alder (NEDDA)反应和反电子需求的Diels-Alder (IEDDA)反应

Scheme 3. Normal-electron-demand Diels-Alder (NEDDA) reaction and inverse-electron-demand Diels-Alder (IEDDA) reaction of 2-pyrones

图式4. 2-吡喃酮的Diels-Alder反应在天然产物全合成中的应用

Scheme 4. Aapplications of 2-pyrone-based Diels-Alder reaction in natural product synthesis

图式5. 2-吡喃酮与马来酰亚胺的不对称Diels-Alder反应

Scheme 5. Asymmetric Diels-Alder reactions of 2-pyrones with maleimide

图式6. 2-吡喃酮与苯甲酰丙烯酸酯的不对称Diels-Alder反应

Scheme 6. Asymmetric Diels-Alder reactions of 2-pyrones with benzoylacrylic esters

图式7. 2-吡喃酮与烯酮的不对称Diels-Alder反应

Scheme 7. Asymmetric Diels-Alder reactions of 2-pyrones with enones

图式8. 2-吡喃酮与N-芳基马来酰亚胺的不对称Diels-Alder反应

Scheme 8. Asymmetric Diels-Alder reactions of 2-pyrone with N-phenyl-maleimide

图式9. 2-吡喃酮与硝基烯烃的不对称Diels-Alder反应

Scheme 9. Asymmetric Diels-Alder reactions of 2-pyrones with nitroalkenes

图式10. 2-吡喃酮与环戊烯-1,3-二酮的不对称Diels-Alder反应

Scheme 10. Asymmetric Diels-Alder reactions of 2-pyrones with cyclopentendiones

图式11. (+)-iso-A82775C的不对称全合成

Scheme 11. Asymmetric total synthesis of (+)-iso-A82775C

图式12. (+)-calvicularin的不对称全合成

Scheme 12. Aymmetric total synthesis of (+)-calvicularin

图式13. 共同中间体50的合成

Scheme 13. Synthesis of common intermediate 50

图式14. Crotophorbolone, langduin A, prostratin, resiniferatoxin和tinyatoxin的全合成

Scheme 14. Total synthesis of crotophorbolone, langduin A, prostratin, resiniferatoxin and tinyatoxin

图式15. 2-吡喃酮的首例不对称反电子需求的Diels-Alder反应

Scheme 15. First examples of IEDDA reactions of 2-pyrones

图式16. 骨钙三醇的不对称合成

Scheme 16. Asymmetric total synthesis of calcitriol

图式17. 铜催化的2-吡喃酮与烯基硒基醚的不对称反电子需求的Diels-Alder反应

Scheme 17. Cu-catalyzed asymmetric IEDDA reaction of 2-pyrones and vinylselenides

图式18. 手性环己二烯-cis-二醇的对映选择性合成

Scheme 18. Asymmetric synthesis of arene cis-dihydrodiols

图式19. cis-十氢合萘的不对称合成

Scheme 19. Asymmetric synthesis of cis-decalins

图式20. 轴手性联芳基化合物的不对称合成

Scheme 20. Asymmetric synthesis of axially chiral biaryls

图式21. 2-吡喃酮与环状2,5-二烯酮的不对称Diels-Alder反应

Scheme 21. Asymmetric Diels-Alder reactions of 2-pyrones with cyclic 2,5-dienones

图式22. 2-吡喃酮与α,β-不饱和醛的不对称Diels-Alder反应

Scheme 22. Asymmetric Diels-Alder reactions of 2-pyrones with α,β-unsaturated aldehydes

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