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

• DOI: 10.1021/acs.orglett.5c00223
• Publication Date: 2025-02-20T11:40:26Z
• Authors: Yifan Zhang; Shuang Li; Hongzhu Chen; Wei Song; Yongquan Ning; Zeyun Liu; Yong Wu; Karunanidhi Murali; Paramasivam Sivaguru; Xiaolong Zhang
• Keywords: Reactivity

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 carbene reactivity DMHz-Tfs iron-catalyzed cyclopropanation Doyle-Kirmse reactions, providing access to diverse acetal functionalized cyclopropanes homoallylic- allenyl-sulfides at gram-scale with high stereoselectivity. DFT calculations elucidated involvement most stable doublet spin state iron-carbene intermediate over other possible states.