Issue 48, 2022, Issue in Progress
From the journal:

RSC Advances

Synthesis of novel chiral spiro-β-lactams from nitrile oxides and 6-(Z)-(benzoylmethylene)penicillanate: batch, microwave-induced and continuous flow methodologies†

Américo J. S. Alves, ORCID logo a   João A. D. Silvestre ORCID logo a  and  Teresa M. V. D. Pinho e Melo ORCID logo *a  

* Corresponding authors

a University of Coimbra, Coimbra Chemistry Centre-Institute of Molecular Sciences and Department of Chemistry, 3004-535 Coimbra, Portugal
E-mail: tmelo@ci.uc.pt

Abstract

The first examples of the diastereoselective 1,3-dipolar cycloaddition reaction of nitrile oxides and 6-alkylidene penicillanates leading to chiral spiroisoxazoline-penicillanates are reported. The synthesis of this new type of penicillanate involved the selective generation of two consecutive stereogenic centers, including a quaternary chiral center. Furthermore, the present work also describes the outcomes of these 1,3-dipolar cycloaddition reactions under three distinct reaction conditions (conventional heating, microwave irradiation and continuous flow). The successful use of the continuous flow technique as well as the proper selection of the reaction media allowed the development of a sustainable route to chiral spiroisoxazoline-penicillanates.

Graphical abstract: Synthesis of novel chiral spiro-β-lactams from nitrile oxides and 6-(Z)-(benzoylmethylene)penicillanate: batch, microwave-induced and continuous flow methodologies

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Article information

DOI
https://doi.org/10.1039/D2RA04848E
Article type
Paper
Submitted
03 Aug 2022
Accepted
16 Oct 2022
First published
28 Oct 2022
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2022,12, 30879-30891

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Synthesis of novel chiral spiro-β-lactams from nitrile oxides and 6-(Z)-(benzoylmethylene)penicillanate: batch, microwave-induced and continuous flow methodologies

A. J. S. Alves, J. A. D. Silvestre and T. M. V. D. Pinho e Melo, RSC Adv., 2022, 12, 30879 DOI: 10.1039/D2RA04848E

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