Please use this identifier to cite or link to this item: http://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: http://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

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