手性膦催化的氮杂环合成研究进展

doi:10.6023/cjoc202208024

摘要/Abstract

手性氮杂环是一类重要的有机分子, 这类骨架广泛存在于药物、农药以及许多具有生物活性的天然产物分子中, 手性含氮杂环的合成是有机合成化学中的重要研究领域, 有机催化反应是合成氮杂环的重要方法, 在这些方法中, 手性有机膦催化的氮杂环的合成被证明是一个实用且强大的方法. 对近年来手性膦催化的氮杂环的合成反应进行了综述, 并对该领域的发展方向进行了展望.

关键词: 手性膦催化剂, 有机催化, 环化反应, 手性氮杂环

Chiral aza-heterocycles are important molecular skeletons of organic chemistry, which are extensively found in pharmaceuticals, pesticides and biologically active natural products. As a significant organic chemistry research filed, the development of efficient novel synthetic methods of them has been a challenge. Among these strategies for the synthesis of aza-heterocycles compounds, chiral phosphine organocatalysis provides a practical and powerful platform. The recent progress in synthesis of chiral nitrogen heterocycles catalyzed by chiral phosphine is summarized, and the development of this field is also prospected.

Key words: chiral phosphine catalyst, organocatalysis, annulation reaction, chiral N-heterocycle

引用此文

任红霞, 马萌萌, 黄有. 手性膦催化的氮杂环合成研究进展[J]. 有机化学, 2022, 42(10): 3129-3142.

Hongxia Ren, Mengmeng Ma, You Huang. Progress in Synthesis of Nitrogen Heterocycles Catalyzed by Chiral Phosphine[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3129-3142.

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图/表 33

图式1. 手性膦催化的烯酮和N-Ts亚胺的[2+2]环化反应

Scheme 1. Chiral phosphine catalyzed [2+2] annulations of ketenes with N-Ts imines

图式2. 手性膦催化的联烯酸酯和亚胺之间的[3+2]环化反应

Scheme 2. Chiral phosphine catalyzed [3+2] annulations of imines with allenoates

图式3. 含硫脲手性膦催化的[3+2]环化反应

Scheme 3. Chiral phosphinothiourea catalyzed [3+2] annulations of imines

图式4. 手性酸-碱膦催化剂催化的活化烯烃与N-Ts亚胺的aza-MBH domino反应

Scheme 4. Chiral acid-base phosphine catalyzed aza-MBH domino reaction of alkenes and N-tosylimines

图式5. 手性膦催化的联烯酸酯与亚胺的[3+2]反应合成天然产物前体

Scheme 5. Chiral phosphine catalyzed [3+2] annulations of allenes with imines for synthesis precursors of natural products

图式6. 膦催化的氮亲核试剂分子内γ加成反应

Scheme 6. Phosphine catalyzed intramolecular γ-addition of nitrogen nucleophiles

图式7. 双功能化膦催化剂催化的环亚胺的[3+2]环化反应

Scheme 7. Bifunctional phosphine catalyzed [3+2] annuluations reaction of cyclic imines

图式8. 羟基脯氨酸衍生的膦催化剂催化的[3+2]环化反应

Scheme 8. Hydroxyproline-derived phosphine catalyzed [3+2] annulations reaction

图式9. 螺环手性膦催化剂催化联烯酸酯的[4+1]环化反应及分子内[3+2]环化反应

Scheme 9. Spiro chiral phosphine catalyzed [4+1] annulations reaction of β'-acetoxy allenoates and intramolecular [3+2] annulations reaction

图式10. 膦催化的酮亚胺和联烯酸酯的[3+2]环化反应

Scheme 10. Phosphine catalyzed [3+2] annuluations reaction with ketimines and allenoates

图式11. 手性膦催化剂催化的[3+2]反应及分子内Rauhut- Currier反应

Scheme 11. Phosphine-catalyzed [3+2] annulations reaction and intramolecular Rauhut-Currier reaction

图式12. 膦催化的联烯酸酯和β-羰基酰胺[3+2]环化反应

Scheme 12. Phosphine catalyzed [3+2] annulations reaction of allenoates and β-carbonyl amides

图式13. P-手性膦氧-膦催化的MBH碳酸酯和α,β-不饱和亚胺之间的[1+4]环化反应

Scheme 13. [1+4] annulation of α,β-unsaturated imines with MBH carbonates catalyzed by P-chiral phosphine oxide-phosphine

图式14. 膦催化的联烯酸酯和N-Ts亚胺的[3+2]环化反应

Scheme 14. Phosphine catalyzed [3+2] annulations reaction of allenoates and N-Ts imines

图式15. 膦催化的MBH碳酸酯和α,β-不饱和亚胺的[1+4]对映选择性环化反应

Scheme 15. Phosphine catalyzed enantioselective [1+4] annulation of MBH carbonates with α,β-unsaturated imines

图式16. 手性双功能双膦催化的羟吲哚和炔酮对映选择性串联Miachel加成反应

Scheme 16. Chiral bifunctional bisphosphine catalyzed enantioselective tandem Michael addition of oxindoles and ynones

图式17. 膦催化的不对称二氮烯加成反应

Scheme 17. Phosphine catalyzed asymmetric cycloaddition reaction of diazenes

图式18. 膦催化的[8+2]环化反应

Scheme 18. Phosphine catalyzed [8+2] annuluations reaction

图式19. 膦催化的立体选择性连续环化反应

Scheme 19. Phosphine catalyzed stereoselective tandem annulation reaction

图式20. 膦催化烯丙胺和γ-取代的联烯酸酯的不对称连续异构化/环化反应

Scheme 20. Phosphine-catalyzed asymmetric tandem isomerization/annulation of allyl amines with γ-substituted allenoates

图式21. 手性膦催化联烯酸酯和亚胺的[4+2]环化反应

Scheme 21. Chiral phosphine catalyzed [4+2] annulation of allenes with imines

图式22. 手性膦催化的aza-Rauhut-Currier [4+2]环化反应

Scheme 22. Chiral phosphine catalyzed aza-Rauhut-Currier [4+2] annulation reaction

图式23. 手性膦催化的分子内[4+2]环化反应

Scheme 23. Chiral phosphine catalyzed intramolecular [4+2] annulation reaction

图式24. 手性硫脲膦催化的分子内[4+2]环化反应

Scheme 24. Chiral thiourea-phosphine catalyzed intramolecular [4+2] annulation reaction

图式25. 手性膦催化的酮亚胺和联烯酸酯的[4+2]环化反应

Scheme 25. Chiral phosphine catalyzed [4+2] annulation reaction of ketimines and allenes

图式26. 手性膦催化的[3+2]环化反应合成六元氮杂环

Scheme 26. Synthesis of six-membered nitrogen heterocycles by chiral phosphine-catalyzed [3+2] annulations reaction

图式27. 手性膦催化的MBH碳酸酯和亚胺的[3+3]环化反应

Scheme 27. Chiral phosphine catalyzed [3+3] annulation reaction of the MBH carbonates with imines

图式28. 手性膦催化的[4+2]/[2+2]环化反应

Scheme 28. Chiral phosphine catalyzed [4+2]/[2+2] cyclizations

图式29. 手性膦催化的分子内Rauhut-Currier反应

Scheme 29. Chiral phosphine catalyzed intramolecular Rauhut-Currier reaction

图式30. 膦催化连续的[4+2]环化反应

Scheme 30. Sequential phosphine-catalyzed [4+2] annulation reaction

图式31. 手性膦催化的[4+2]环化反应

Scheme 31. Chiral phosphine catalyzed [4+2] annulations reaction

图式32. 手性膦催化剂参与催化的[4+3]环化反应

Scheme 32. Chiral phosphine catalyzed [4+3] annulation reaction

图式33. 手性膦催化剂参与催化的[4+4]环化反应

Scheme 33. Chiral phosphine catalyzed [4+4] annulations reaction

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