Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines-Reference-Cited by-同舟云学术

Asymmetric Neber Reaction in the Synthesis of Chiral 2-(Tetrazol-5-yl)-2H-Azirines

Published:2019-12-17 Issue:06 Volume:31 Page:553-558
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Alves Cláudia¹^ORCID,Grosso Carla¹^ORCID,Barrulas Pedro²³^ORCID,Paixão José A.⁴^ORCID,Cardoso Ana L.¹^ORCID,Burke Anthony J.²^ORCID,Lemos Américo¹⁵^ORCID,Pinho e Melo Teresa M. V. D.¹^ORCID

Affiliation:

1. CQC and Department of Chemistry, University of Coimbra, 3004-535 Coimbra

2. Centro de Química de Évora and Department of Chemistry, University of Évora

3. HERCULES Laboratory, Évora University

4. CFisUC and Department of Physics, University of Coimbra

5. FCT, University of Algarve

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.

Funder

Fundação para a Ciência e a Tecnologia

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0039-1691533.pdf

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1. Selective Synthesis of 3-(1H-Tetrazol-5-yl)-indoles from 2H-Azirines and Arynes;ACS Omega;2024-06-24

2. Organocatalysts for the Asymmetric Neber reaction: Synthesis of Chiral 2‐(Tetrazol‐5‐yl)‐2H‐Azirines;ChemistrySelect;2023-09-19

3. Enantioselective C–C, C–halogen and C–H bond forming reactions promoted by organocatalysts based on non-proteinogenic α-amino acid derivatives;Enantioselective C-C Bond Forming Reactions: From Metal Complex-, Organo-, and Bio-catalyzed Perspectives;2023

4. Synthesis of various functionalized 2 H ‐azirines: An updated library;Journal of Heterocyclic Chemistry;2021-12-15

5. Synthesis of 2-(2-Pyridyl)-2H-azirines via Metal-Free C–C Cross-Coupling of Bromoazirines with 2-Stannylpyridines;Organic Letters;2021-10-01