Advances in organocatalytic asymmetric [3 + 3] cycloadditions: synthesis of chiral six-membered (hetero)cyclic compounds

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(19), P. 5573 - 5604

Published: Jan. 1, 2024

This review has summarized the development of organocatalytic asymmetric [3 + 3] cycloadditions and given insights into remaining challenges to promote future this field.

Language: Английский

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Organocatalytic Asymmetric Michael Reactions of Cyclic N-Sulfonylimines with Nitroalkenes or 2-Nitroallylic Acetates

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 25, 2025

A highly efficient enantioselective Michael addition of cyclic N-sulfonylimines with nitroalkenes has been developed, utilizing a bifunctional squaramide catalyst. This approach achieves remarkable results, delivering products high yields and outstanding stereoselectivities, reaching up to 97% yield, >20:1 dr, >99% ee. Furthermore, an asymmetric tandem reaction 2-nitroallylic acetates established. innovative methodology involves Michael/intramolecular aza-Michael cascade, leading the formation enantioenriched benzosultam-fused tricyclic compounds excellent stereoselectivities (up dr ee).

Language: Английский

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Phosphine vs DBU-Catalyzed Annulation Reactions of β′-Acetoxy Allenoates with Acyl-Tethered Benzothiazole Bisnucleophiles: (4 + 3) or (4 + 1) vs (3 + 3) Annulation

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10816 - 10830

Published: July 15, 2024

Dearomative annulation reaction of acyl-tethered benzothiazole bisnucleophiles with β'-acetoxy allenoates by switching the Lewis base is developed. The DBU-catalyzed gives benzothiazole-fused 1,4-dihydropyridine carboxylates (3 + 3) chemoselectively. By contrast, PR

Language: Английский

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