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Synthesis 2021; 53(16): 2865-2873
DOI: 10.1055/a-1503-8068
DOI: 10.1055/a-1503-8068
paper
Lewis Acid Mediated [3+2] and [3+3] Annulations of an Azomethine Imine with Donor–Acceptor Cyclopropanes
Abstract
Two different Lewis acids were used for developing [3+2] and [3+3] regioselective cycloaddition reactions of an azomethine imine with activated cyclopropanes. Scandium(III) triflate catalyzes a [3+2] cycloaddition reaction of the azomethine imine with cyclopropanes to form tetrahydropyrazolone derivatives and tricyclic tetrahydrofuran derivatives in moderate yields. Complementary to this, a novel [3+3] cycloaddition reaction of the azomethine imine with activated cyclopropanes was developed by using EtAlCl2 as a Lewis acid to form hexahydropyridazinone derivatives in high regioselectivity.
Key words
pyrazolidines - [3+2] cycloaddition - [3+3] cycloaddition - azomethine imines - donor–acceptor cyclopropanesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1503-8068.
- Supporting Information
- CIF File
Publikationsverlauf
Eingereicht: 18. März 2021
Angenommen nach Revision: 10. Mai 2021
Accepted Manuscript online:
10. Mai 2021
Artikel online veröffentlicht:
10. Juni 2021
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