B(c6f5)3-catalyzed diastereoselective and divergent reactions of vinyldiazo esters with nitrones: synthesis of highly functionalized diazo compounds

Stefkova, Katarina, Guerzoni, Michael G., van Ingen, Yara, Richards, Emma ORCID: https://orcid.org/0000-0001-6691-2377 and Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 2023. B(c6f5)3-catalyzed diastereoselective and divergent reactions of vinyldiazo esters with nitrones: synthesis of highly functionalized diazo compounds. Organic Letters 25 (3) , pp. 500-505. 10.1021/acs.orglett.2c04198

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Abstract

Herein we report a mild, transition-metal-free, highly diastereoselective Lewis acid catalyzed methodology toward the synthesis of isoxazolidine-based diazo compounds from the reaction between vinyldiazo esters and nitrones. Interestingly, the isoxazolidine products were identified to have contrasting diastereoselectivity to previously reported metal-catalyzed reactions. Furthermore, the same catalyst can be used with enol diazo esters, prompting the formation of Mukaiyama–Mannich products. These diazo products can then be further functionalized to afford benzo[b]azepine and pyrrolidinone derivatives.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Schools > Chemistry Research Institutes & Centres > Cardiff Catalysis Institute (CCI)
Publisher:	American Chemical Society
ISSN:	1523-7060
Funders:	EPSRC, Leverhulme Trust
Date of First Compliant Deposit:	13 January 2023
Date of Acceptance:	9 January 2023
Last Modified:	01 Jul 2023 17:34
URI:	https://orca.cardiff.ac.uk/id/eprint/155828

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