Rhodium‐Catalyzed One‐Carbon Ring Expansion of Aziridines with Vinyl‐N‐triftosylhydrazones for the Synthesis of 2‐Vinyl Azetidines

Author:

Ning Yongquan1,Chen Hongzhu1,Ning Yongyue1,Zhang Jin1,Bi Xihe12ORCID

Affiliation:

1. Department of Chemistry Northeast Normal University 130024 Changchun China

2. State Key Laboratory of Elemento-Organic Chemistry Nankai University 300071 Tianjin China

Abstract

AbstractAzetidines, being four‐membered N‐heterocycles, possess significant potential in contemporary medicinal chemistry owing to their favorable pharmacokinetic properties. Regrettably, the incorporation of functionalized azetidines into pharmaceutical lead structures has been impeded by the absence of efficient synthetic methods for their synthesis. In this study, a Rh‐catalyzed one‐carbon ring expansion of aziridines with vinyl‐N‐triftosylhydrazones is presented, which facilitates the synthesis of high value‐added 2‐alkenyl azetidine products. This research represents the first example of ring expansion of aziridines enabled by vinyl carbenes. Additionally, a one‐pot two‐step protocol, initiated from cinnamaldehyde, was successfully achieved, offering a step‐economical and facile approach for the synthesis of these compounds. The pivotal aspect of this successful transformation lies in the in situ formation of an alkenyl aziridinium ylide intermediate. Experimental investigations, coupled with computational studies, suggest that a diradical pathway is involved in the reaction mechanism.

Funder

National Natural Science Foundation of China

Department of Science and Technology of Jilin Province

Publisher

Wiley

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