1. Asymmetric neber reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines
- Author
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Teresa M. V. D. Pinho e Melo, Cláudia Alves, Ana L. Cardoso, Américo Lemos, Anthony J. Burke, Pedro Barrulas, José A. Paixão, and Carla Grosso
- Subjects
6β-aminopenicillanic acid ,010405 organic chemistry ,Organic Chemistry ,asymmetric Neber reaction ,010402 general chemistry ,01 natural sciences ,Combinatorial chemistry ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,Chemistry ,Thiourea ,chemistry ,Organocatalysis ,organocatalysis ,6 beta-aminopenicillanic acid ,2H-azirines ,thiourea ,tetrazoles - Abstract
A successful one-pot methodology for the synthesis of chiral 2-tetrazolyl-2H-azirines has been established, resorting to organocatalysis. The protocol involves the in situ tosylation of beta-ketoxime-1H-tetrazoles followed by the Neber reaction, in the presence of chiral organocatalysts. Among the organocatalysts studied a novel thiourea catalyst derived from 6 beta-aminopenicillanic acid afforded excellent enantioselectivities. Portuguese Agency for Scientific Research, 'Fundacao para a Ciencia e a Tecnologia' (FCT) [UID/QUI/00313/2019] FCTPortuguese Foundation for Science and TechnologyEuropean Commission [SFRH/BD/130198/2017] Evora Chemistry Centre (CQE) through the strategic FCT project [Pest-OE/QUI/UI0619/2019] [PD/BD/143159/2019] info:eu-repo/semantics/publishedVersion
- Published
- 2020