Dimethoxyacetaldehyde-N-triftosylhydrazone: Preparation and Carbene Reactivity in Cyclopropanation and Doyle-Kirmse Reactions.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-28 Epub Date: 2025-02-20 DOI:10.1021/acs.orglett.5c00223

Yifan Zhang, Shuang Li, Hongzhu Chen, Wei Song, Yongquan Ning, Zeyun Liu, Yong Wu, Karunanidhi Murali, Paramasivam Sivaguru, Xiaolong Zhang

引用次数: 0

Abstract

Herein, we developed the new, powerful, and easy-to-handle chemical reagent, dimethoxyacetaldehyde-N-triftosylhydrazone (DMHz-Tfs), as a convenient in situ source of dimethoxydiazoethane under mild conditions. We demonstrate the carbene reactivity of DMHz-Tfs in iron-catalyzed cyclopropanation and Doyle-Kirmse reactions, providing access to diverse acetal functionalized cyclopropanes and homoallylic- and allenyl-sulfides at gram-scale with high stereoselectivity. DFT calculations elucidated the involvement of the most stable doublet spin state iron-carbene intermediate over other possible spin states.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.