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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Cobalt-Catalyzed Regioselective Hydroxyazidation of 1,3-Dienes: Direct Access to β-Azido Alcohols
Chi-Fan Zhu1, Xiao-Jing Li1, Jun-Ju Mai1
1School of Pharmacy, Changzhou University, Changzhou, Jiangsu 213164, China.
Abstract:
A cobalt-catalyzed stereoselective 1,2-hydroxyazidation of 1,3-dienes has been developed, enabling efficient synthesis of β-azido alcohols, which retain a C═C bond for further derivatization. This protocol features a broad substrate scope, employs an inexpensive cobalt catalyst, and proceeds under ambient air at room temperature. The method offers direct access to valuable β-azido alcohols, which serve as key precursors to β-amino alcohols and various nitrogen/oxygen-containing heterocycles. Mechanistic investigations revealed the hydroxyl group origin and provided evidence for a radical-based pathway.
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