羟胺衍生物的[3,3] σ迁移反应及其应用

doi:10.6023/cjoc202103022

摘要/Abstract

[3,3] σ迁移反应作为有机化学中的经典反应, 自发现以来, 反应类型不断扩大, 且一直广泛应用于有机与药物合成等领域. 因为羟胺衍生物的N—O键强度较弱, 较易断裂, [3,3] σ迁移反应在较为温和的条件下即可进行, 得到含有羟基和氨基的复杂分子, 近年来, 该类反应引起越来越多的关注. 综述了羟胺衍生物的[3,3] σ迁移反应, 包括N-芳

关键词: [3,3] σ迁移, 羟胺衍生物, 重排, 亲核反应, N—O键

[3,3] σ shift is one of classic reactions in organic chemistry. Since its discovery, the reactions have been expanding to different types and widely used in the fields of organic and pharmaceutical synthesis. Because the N—O bond strength of hydroxylamine derivatives is weak and easy to break, their [3,3] σ shift can be carried out under mild conditions to afford complex molecules containing hydroxyl and amino groups. In recent years, more and more attention has been paid to these reactions. The [3,3] σ shift rearrangements of hydroxylamine derivatives, including N-aryl-O-alkenylhydroxylamines, N,O-diaryl hydroxylamines, N,O-dialkenyloxyamines, N-alkenyl-O-arylhydroxyamines, and N-alkyl-O-acylhydroxyamines are reviewed, and a new prospect for the [3,3] σ shifts of hydroxylamine derivatives and their future development are put forward.

Key words: [3,3] σ shift, hydroxylamine, rearrangement, nucleophilic reaction, N—O bond

引用此文

张广宇, 许家喜. 羟胺衍生物的[3,3] σ迁移反应及其应用[J]. 有机化学, 2021, 41(8): 3002-3014.

Guangyu Zhang, Jiaxi Xu. [3,3] Sigmatropic Shifts and Applications of Hydroxylamine Derivatives[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3002-3014.

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图/表 35

图式1. Bartoli吲哚合成

Scheme 1. Bartoli indole synthesis

图式2. 改进的Bartoli吲哚合成

Scheme 2. Improved Bartoli indole synthesis

图式3. O-环丙基羟胺的[3,3] σ迁移反应

Scheme 3. [3,3] σ shift of O-cyclopropyl hydroxylamine

图式4. N-Boc-2-羟基四氢喹啉的进一步功能化

Scheme 4. Further functionalizations of N-Boc-2-hydroxy- tetrahydroquinoline

图式5. 几种重要的含有氨基和羟基的联芳类化合物

Scheme 5. Several important biaryl compounds with amino and hydroxyl groups

图式6. 杂环参与的[3,3] σ迁移反应

Scheme 6. [3,3] σ shift involving heteroaryl group

图式7. 2-氨基-3-溴-2'-羟基-1,1'-联苯的合成

Scheme 7. Synthesis of 2-amino-3-bromo-2'-hydroxy-1,1'- biphenyl

图式8. N,O-二芳基羟胺的[3,3] σ迁移反应

Scheme 8. [3,3] σ shift of N,O-diarylhydroxyamines

图式9. 芳基羟胺的芳香亲核取代及重排反应

Scheme 9. Nucleophilic aromatic substitution and rearrangement of arylhydroxylamines

图式10. 通过二芳基碘鎓盐合成NOBIN型化合物

Scheme 10. Synthesis of NOBIN-type products from diaryliodonium salts.

图式11. 通过二萘基碘鎓盐合成NOBIN型化合物

Scheme 11. Synthesis of NOBIN-type products from dinaphthyliodonium salts.

图式12. 通过芳基季铵盐合成NOBIN型化合物

Scheme 12. Synthesis of NOBIN-type products from arylammonium salts

图式13. 通过芳基季铵盐合成NOBIN型化合物

Scheme 13. Synthesis of NOBIN-type products from arylam- monium salts

图式14. NHC催化的消旋NOBIN型化合物的动力学拆分

Scheme 14. NHC-catalyzed kinetic resolution of racemic NOBIN-type product

图式15. NOBIN型化合物的合成应用

Scheme 15. Synthetic applications of the NOBIN-type product

图式16. N-烯基羟胺的制备

Scheme 16. Synthesis of N-alkenylhydroxylamine

图式17. 2-氨基四氢呋喃类化合物的合成

Scheme 17. Synthesis of 2-aminotetrahydrofuran derivative

图式18. N,O-二烯基羟胺的[3,3] σ迁移反应机理

Scheme 18. Mechanism on [3,3] σ shift of N,O-dialkenylhy- droxyamine

图式19. 通过[3,3] σ迁移合成螺环1-吡咯啉

Scheme 19. Synthesis of spirocyclic 1-pyrrolines through [3,3] σ shift

图式20. Boekelheide重排

Scheme 20. Boekelheide rearrangement

图式21. 环己酮的α-位酰氧基化

Scheme 21. α-Acyloxylation of cyclohexanone

图式22. 3-甲基丁醛的α-位酰氧基化

Scheme 22. α-Acyloxylation of 3-methylbutyraldehyde

图式23. 醛α-位酰氧基化机理

Scheme 23. Mechanism of α-acyloxylation of aldehydes

图式24. 经N-酰氧基烯胺的[3,3] σ迁移

Scheme 24. [3,3] σ shift via N-acyloxyenamine

图式25. 经N-酰氧烯胺[3,3] σ迁移反应的量子化学计算

Scheme 25. Quantum-chemical calculations for [3,3] σ shift via N-acyloxyenamine

图式26. 两种不同的[3,3] σ迁移

Scheme 26. Two different [3,3] σ shifts

图式27. 通过原酸酯立体选择性合成α-羟基酯

Scheme 27. Stereoselective synthesis of α-hydroxy esters from ortho esters

图式28. 通过原酸酯立体选择性合成α-羟基酯的机理

Scheme 28. Mechanism on the stereoselective synthesis of α- hydroxy esters from ortho esters

图式29. 立体选择性合成α-羟基酯[3,3] σ迁移反应中的两种过渡态

Scheme 29. Two transition states in [3,3] σ shift for the stereoselective synthesis of α-hydroxy esters

图式30. N-酰氧基-N-烯基酰胺在不同条件下的[3,3] σ迁移反应

Scheme 30. [3,3] σ shifts of N-acyloxy-N-alkenylamides under different conditions

图式31. 2-甲基喹啉N-氧化物的磷酸化

Scheme 31. Phosphorylation of 2-methylquinoline N-oxide

图式32. 推测的2-甲基喹啉N-氧化物磷酸化的机理

Scheme 32. Proposed mechanism on phosphorylation of 2-methylquinolin N-oxide

图式33. 硝酮的磷酸化

Scheme 33. Phosphorylation of nitrone

图式34. 苯乙酮的直接α-磷酰氧基化

Scheme 34. Direct α-phosphoryloxylation of acetophenone

图式35. 通过α-羟基膦酸酯的[1,2]重排反应制备β-羰基醇磷酸酯

Scheme 35. Synthesis of β-ketoalkyl phosphate via [1,2]rearran- gement of α-hydroxyalkylphosphonate

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