Iodobenzene-Catalyzed Oxidative Cyclization for the Synthesis of Highly Functionalized Cyclopropanes

Yang Li; Hao Guo; Renhua Fan

doi:10.1055/s-0039-1690809

Synthesis, Table of Contents

Synthesis 2020; 52(06): 928-932
DOI: 10.1055/s-0039-1690809

paper

Iodobenzene-Catalyzed Oxidative Cyclization for the Synthesis of Highly Functionalized Cyclopropanes

Yang Li

,

Hao Guo∗

,

Renhua Fan∗

Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, P. R. of China Email: rhfan@fudan.edu.cn

› Author Affiliations

Abstract

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Abstract

An iodobenzene-catalyzed oxidative cyclization of Michael adducts of activated methylene compounds with nitroolefins or chalcones is developed. mCPBA is used as oxidant together with Bu₄NI for the generation of a highly reactive iodine(III) species to mediate the cyclopropanation via a ligand exchange and reductive elimination process. A range of highly functionalized cyclopropanes are synthesized with high diastereoselectivities.

Key words

iodobenzene - cyclization - cyclopropane - iodine - oxidation

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