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Updated: Nov 26, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Nitroxyl Catalysts for Six-Membered Ring Bromolactonization and Intermolecular Bromoesterification of Alkenes with
Katsuhiko Moriyama1, Masako Kuramochi1, Seiji Tsuzuki2
1Department of Chemistry, Graduate School of Science and Soft Molecular Activation Research Center, Chiba University 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Abstract:
We developed a nitroxyl-catalyzed bromoesterification of alkenes with bromo reagents, which includes a six-membered ring bromolactonization of alkenyl carboxylic acids catalyzed by AZADO as the nitroxyl radical catalyst, and an intermolecular bromoesterification of alkenes with carboxylic acids using NMO as the N-oxide catalyst. We also accomplished a remote diastereoselective bromohydroxylation via an AZADO-catalyzed six-membered ring bromolactonization and a subsequent ring cleavage reaction with alkylamines to furnish ε-bromo-δ-hydroxy amides with high diastereoselectivity.
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