Progress in the Construction of Functionalized Derivatives Based on Dihydropyran Skeleton Modification

doi:10.6023/cjoc202502005

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (6): 1920-1945.DOI: 10.6023/cjoc202502005 Previous Articles Next Articles

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基于二氢吡喃骨架修饰构建其官能化衍生物的研究进展

魏泽齐^†, 孙鑫浩^†, 黎思瑞, 宋汪泽^*()

大连理工大学化学学院辽宁大连 116024

收稿日期:2025-02-04 修回日期:2025-03-24 发布日期:2025-04-24
通讯作者: 宋汪泽
作者简介:
^†共同第一作者.
基金资助:
中央高校基本科研业务费(DUT24YG125); 中央高校基本科研业务费(DUT24ZD114); 中央高校基本科研业务费(2023JH2/101700293); 国家大学生创新创业训练计划(20251014110007)

Progress in the Construction of Functionalized Derivatives Based on Dihydropyran Skeleton Modification

Zeqi Wei^†, Xinhao Sun^†, Sirui Li, Wangze Song^*()

School of Chemistry, Dalian University of Technology, Dalian, Liaoning 116024

Received:2025-02-04 Revised:2025-03-24 Published:2025-04-24
Contact: Wangze Song
About author:
^†The authors contributed equally to this work.
Supported by:
Fundamental Research Funds for the Central Universities(DUT24YG125); Fundamental Research Funds for the Central Universities(DUT24ZD114); Fundamental Research Funds for the Central Universities(2023JH2/101700293); National College Students’ Innovation and Entrepreneurship Training Program(20251014110007)

Dihydropyran compounds are one of oxygen-containing heterocyclic compounds widely existing in natural products and have a wide range of biological activities. They are also important synthetic precursors of carbohydrate compounds and some natural products. Therefore, it is of great significance to study the synthesis of these compounds and their derivatives. According to the different dihydropyran products, this review mainly focuses on the research progress in the synthesis of dihydropyran derivatives substituted by oxygen-, carbon-and nitrogen-based groups, and discusses the related mechanism and application range of related reactions.

Key words: dihydropyrans, oxygen-based dihydropyran derivatives, carbon-based dihydropyran derivatives, nitrogen-based dihydropyran derivatives

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Zeqi Wei, Xinhao Sun, Sirui Li, Wangze Song. Progress in the Construction of Functionalized Derivatives Based on Dihydropyran Skeleton Modification[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1920-1945.

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Fig. & Tab. 76

Figure 1. Structure of dihydropyrans and bioactive dihydropyran derivatives

Scheme 1. Two main methods for the synthesis of dihydropyran derivatives

Scheme 2. Re-catalyzed the synthesis of oxyglycoside compounds

Scheme 3. Pd-catalyzed stereoselective synthesis of dihydropyran derivatives

Scheme 4. Pd-catalyzed stereoselective synthesis of α-O-glyco-sides

Scheme 5. Au-catalyzed synthesis of dihydropyranyl oxygen derivatives

Scheme 6. Pd-catalyzed stereoselective synthesis of 3-deoxy-glycosides from dihydropyrans

Scheme 7. Pd-catalyzed α‑stereoselective O‑glycosylation of 3-O‑acylated glycals

Scheme 8. Pd(0) and Pd(Ⅱ)-catalyzed stereoselective O-glycosylation

Scheme 9. Au-catalyzed stereoselective synthesis of 3-deoxyglycosides

Scheme 10. Temperature and Brønsted acid-controlled the trans-formation of silyl protected rhamnals

Scheme 11. Pd-catalyzed stereoselective O-glycosylation of glycals with arylboronic acids using air as the oxidant

Scheme 12. Pd-catalyzed stereodivergent O-glycosylation of glycals and alcohols

Scheme 13. Pd-catalyzed the synthesis of 3,4-dihydropyranoneoxy derivatives

Scheme 14. Synthesis of 3,4-dihydropyranone derivatives from the products of Achmatowicz rearrangement

Scheme 15. Pd-catalyzed synthesis of oligopyranone derivatives

Scheme 16. Lewis acid-catalyzed the glycosidation

Scheme 17. Pd-catalyzed reaction of D-tyrosine and dihydropyranones

Scheme 18. Synthesis of dihydropyranone derivatives derived from perbenzylated kaempferol

Scheme 19. Chemoselective glycosylations using 3,4-dihydropyranone derivatives

Scheme 20. Pd-ctalyzed kinetic resolution of allylic esters

Scheme 21. Base-promoted synthesis of bicyclic acetal compound

Scheme 22. DKEAT of dihydropyranones

Scheme 23. High stereoselective synthesis of oxydihydropyranone derivatives by DKDA method

Scheme 24. NHC-catalyzed dynamic kinetic stereoselective acylation of dihydropyranones

Scheme 25. Au or Ag-catalyzed the synthesis of dihydropyranoneoxy derivatives

Scheme 26. Ir-catalyzed redox isomerization

Scheme 27. Enzyme-catalyzed redox isomerization

Scheme 28. Lewis aicd-catalyzed C-glycosylation with enol-silane as donor

Scheme 29. Pd-catalyzed stereoselective C-glycosidation of glycals with arylboronic acids

Scheme 30. Stereoselective addition reaction between organo-zinc reagents and 2,3-dihydropyrans

Scheme 31. Lewis acid-catalyzed nucleophilic addition of acetylenyl potassium trifluoroborate with D-glucose

Scheme 32. Oxidant-controlled Heck-type C-glycosylation of dihydropyrans with arylboronic acids

Scheme 33. Pd-catalyzed Heck coupling reactions of dihydropyrans and aryl iodides

Scheme 34. Microwave-assisted Pd-catalyzed synthesis of C-aryldihydropyrans

Scheme 35. Synthesis of 2-deoxy-C-aryl glycosides by Pd-cata-lyzed decarboxylation

Scheme 36. Pd-catalyzed stereoselective C-glycosylation of di-hydropyrans with enol triflates

Scheme 37. Pd-catalyzed decarboxylation stereoselective synthesis of dihydropyrans

Scheme 38. Pd-catalyzed oxidative Heck reaction of dihydropyrans with arylhydrazine

Scheme 39. “Ring Opening-Ring Closure” strategy for the synthesis of C-aryl glycosides

Scheme 40. TEMPO-promoted domino Heck-Suzuki arylation

Scheme 41. Pd-catalyzed tandem decarboxylative allylation and Wittig reaction

Scheme 42. Au-catalyzed synthesis of vinyl dihydropyran derivatives via tandem 1,3-acyloxy migration and Ferrier rearrangement

Scheme 43. Synthesis of 2-deoxy-C-glycosides using dihydropyrans and aromatic amines

Scheme 44. Ir-catalyzed hydroarylation of dihydropyrans

Scheme 45. Pd-catalyzed stereoselective C-glycosylation of dihydropyrans with coumarins

Scheme 46. Pd-catalyzed stereoselective reaction of dihydropyrans and aromatic diazo salts

Scheme 47. Pd-catalyzed reaction of dihydropyran carbonates and aryl boronic acids

Scheme 48. Other transition metal-catalyzed transformation reactions of dihydropyrans

Scheme 49. Ni-catalyzed transformation reactions of dihydropyrans

Scheme 50. Pd-catalyzed tandem cyclization

Scheme 51. Synthesis of trans-aryl dihydropyranone derivatives by two-step method

Scheme 52. Oxa-[3＋2] cycloaddition of dihydropyranones and cyclic 1,3-dicarbonyl compounds

Scheme 53. Pd-catalyzed [3＋2] C—C/C—N bond-formation annulation

Scheme 54. TFAA-catalyzed the synthesis of trans-dihydro-pyranone derivatives

Scheme 55. Pd-catalyzed coupling reaction of dihydropyrans and aryl boronic acids

Scheme 56. Pd-catalyzed the synthesis of coumarin-dihydro-pyranones derivatives by allyl-allyl coupling

Scheme 57. Palladium-catalyzed N-amination of di-indolectams and dihydropyrans

Scheme 58. Pd-catalyzed N-glycosylation of sulfonamide

Scheme 59. B(C6F5)3-catalyzed N-amination

Scheme 60. BF3·Et2O-catalyzed N-amination

Scheme 61. Pd-catalyzed trichloroimine ester rearrangement

Scheme 62. Ligand-controlled trichloroimine ester rearrangement

Scheme 63. Amberlyst 15-catazlyed N-amination

Scheme 64. ZnCl2/Al2O3-catalyzed N-amination

Scheme 65. Lewis acid-catalyzed synthesis of N-amino enones

Scheme 66. Pd-catalyzed decarboxylative allylation for one-pot synthesis of β-N-imidazolyl dihydropyrans

Scheme 67. I2-promoted aza-Ferrier rearrangement of dihydropyrans with amines

Scheme 68. Ru-catalyzed N-amination

Scheme 69. Zn(OTf)2-catalyzed N-amination

Scheme 70. Pd-catalyzed synthesis of N-amino dihydropyran derivatives

Scheme 71. Er(OTf)3-catalyzed one-pot synthesis of N-amino dihydropyran derivatives

Scheme 72. Pd-catalyzed stereoselective synthesis of β-N-amino dihydropyrans

Scheme 73. Direct N-glycosylation of amides/amines with gly-cal donors

Scheme 74. Pd-catalyzed the synthesis of amino dihydropyranone derivatives

Scheme 75. Brønsted acid-catalyzed the synthesis of sulfoximide substituted dihydropyranone derivatives

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基于二氢吡喃骨架修饰构建其官能化衍生物的研究进展

Progress in the Construction of Functionalized Derivatives Based on Dihydropyran Skeleton Modification

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