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Synthesis 2020; 52(20): 3029-3035
DOI: 10.1055/s-0040-1707193
DOI: 10.1055/s-0040-1707193
paper
Catalyst-Free Synthesis of Diastereomerically Pure 3-Sulfonylazetidin-2-ones via Microwave-Assisted Tandem Wolff Rearrangement–Staudinger Cycloaddition
This research was supported by the Russian Foundation for Basic Research (grant no. 20-03-00922).Further Information
Publication History
Received: 09 May 2020
Accepted after revision: 04 June 2020
Publication Date:
21 July 2020 (online)
Abstract
A wide range of α-diazo-β-ketosulfones have been applied to thermally promoted tandem Wolff rearrangement – Staudinger [2+2] cycloaddition with imines to give polysubstituted β-lactam sulfones. Diastereomerically pure syn-diastereomers were obtained in good yields and the relative stereochemistry was confirmed by single-crystal X-ray crystallography. These findings significantly expand the scope of this transformation, in contrast to substantial limitations reported previously. Moreover, this methodology enables flexible exploration of new substitution patterns around the privileged β-lactam core for drug design and optimization.
Key words
α-diazo-β-ketosulfones - Wolff rearrangement - Staudinger β-lactam synthesis - catalyst free - microwave irradiationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707193.
- Supporting Information
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