Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage

doi:10.6023/cjoc202303026

Abstract

There are two different ring-opening modes of aziridines: ring-opening of aziridines via carbon-nitrogen bond cleavage, and ring-opening of aziridines via carbon-carbon bond cleavage. Among them, the reaction of aziridines via carbon-nitrogen bond cleavage has been reported in many reviews. The cycloaddition reactions of donor-acceptor (D-A) aziridines via carbon-carbon bond cleavage in recent 20 years are mainly summarized. Under some proper catalysts, the ring-opening of D-A aziridines via carbon-carbon bond cleavage yield azomethine ylides, which can undergo [3+n] cycloaddition reaction with aldehydes, imines, alkenes, alkynes, indoles etc.

Key words: D-A aziridines, carbon-carbon bond cleavage, cycloaddition reaction, azomethine ylide

Cite this article

Zuliang Chen, Yingjing Wei, Junliang Zhang. Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3078-3088.

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Fig. & Tab. 24

Scheme 1. Two different ring-opening modes of aziridines

Scheme 2. Lewis acid-promoted carbon-carbon bond cleavage of D-A aziridines

Scheme 3. Y(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with alkenes

Scheme 4. Plausible mechanism of [3+2] cycloaddition reaction of D-A aziridines with alkenes

Scheme 5. Lewis acid-catalyzed intramolecular [3+2] cycloaddition reaction of D-A aziridines with conjugated dienes

Scheme 6. Sc(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with methylene exo-glycals

Scheme 7. Sc(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with alkynes

Scheme 8. Au/Yb(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with alkynyl alcohols/amines

Scheme 9. Lewis Acid-catalyzed [3+2] cycloaddition reaction of D-A aziridines with aldehydes/imines

Scheme 10. Fe(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with indoles

Scheme 11. HOTf-catalyzed [3+2] cycloaddition reaction of D-A aziridines with nitriles

Scheme 12. Y(OTf)3-catalyzed [3+2] cycloaddition reaction of D-A aziridines with 1,3,5-triazinanes

Scheme 13. [3+2] cycloaddition reaction of D-A aziridines with ketenimines

Scheme 14. MgI2-catalyzed [3+3] cycloaddition reaction of D-A aziridines with 1,4-dithiane-2,5-diol

Scheme 15. Gd(OTf)3-catalyzed [3+3] cycloaddition reaction of D-A aziridines with N,N-dialkyl-3-vinylanilines

Scheme 16. [3+3] cycloaddition reaction of D-A aziridines with β-(indol-2-yl)-α,β-unsaturated ketones

Scheme 17. Y(OTf)3-catalyzed [3+1+1] or [3+1] cycloaddition reaction of D-A aziridines with isocyanides

Scheme 18. MgI2-catalyzed cycloaddition of D-A aziridines with D-A cyclopropanes and their mechanism

Scheme 19. Asymmetric [3+2] cycloaddition of D-A aziridines with aldehydes

Scheme 20. Asymmetric [3+2] cycloaddition of D-A aziridines with alkenes

Scheme 21. Asymmetric [3+2] cycloaddition of D-A aziridines with alkynes

Scheme 22. Asymmetric [3+2] cycloaddition of D-A aziridines with indoles

Scheme 23. Asymmetric [3+3] cycloaddition of D-A aziridines with aklkenes

Scheme 24. Asymmetric [3+1] cycloaddition of D-A aziridines with isocyanides

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