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https://hdl.handle.net/10316/90926| Title: | Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines | Authors: | Alves, Cláudia Grosso, Carla Barrulas, Pedro Paixão, José A. Cardoso, Ana L. Burke, Anthony J. Lemos, Américo Melo, Teresa M. V. D. Pinho e |
Keywords: | 2H-azirines; Asymmetric Neber reaction; Organocatalysis; Tetrazoles; Thiourea; 6β-aminopenicillanic acid | Issue Date: | 2019 | Publisher: | Georg Thieme Verlag | Project: | UID/QUI/00313/2019 SFRH/BD/130198/2017 PD/BD/143159/2019 |
Serial title, monograph or event: | Synlett | Volume: | 31 | Issue: | 6 | 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 β-ketoxime-1H-tetrazoles followed by the Neber reaction, in the presence of chiral organocatalysts. Among the organocatalysts studied a novel thiourea catalyst derived from 6β-aminopenicillanic acid afforded excellent enantioselectivities. | URI: | https://hdl.handle.net/10316/90926 | ISSN: | 0936-5214 1437-2096 |
DOI: | 10.1055/s-0039-1691533 | Rights: | embargoedAccess |
| Appears in Collections: | I&D CQC - Artigos em Revistas Internacionais |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| Alves2020Synlett.pdf | 1.94 MB | Adobe PDF | View/Open |
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