[3,3] Sigmatropic Shifts and Applications of Hydroxylamine Derivatives

doi:10.6023/cjoc202103022

Abstract

[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

Cite this article

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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Fig. & Tab. 35

Scheme 1. Bartoli indole synthesis

Scheme 2. Improved Bartoli indole synthesis

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

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

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

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

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

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

Scheme 9. Nucleophilic aromatic substitution and rearrangement of arylhydroxylamines

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

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

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

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

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

Scheme 15. Synthetic applications of the NOBIN-type product

Scheme 16. Synthesis of N-alkenylhydroxylamine

Scheme 17. Synthesis of 2-aminotetrahydrofuran derivative

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

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

Scheme 20. Boekelheide rearrangement

Scheme 21. α-Acyloxylation of cyclohexanone

Scheme 22. α-Acyloxylation of 3-methylbutyraldehyde

Scheme 23. Mechanism of α-acyloxylation of aldehydes

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

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

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

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

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

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

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

Scheme 31. Phosphorylation of 2-methylquinoline N-oxide

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

Scheme 33. Phosphorylation of nitrone

Scheme 34. Direct α-phosphoryloxylation of acetophenone

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

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羟胺衍生物的[3,3] σ迁移反应及其应用