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Synthesis 2020; 52(06): 928-932
DOI: 10.1055/s-0039-1690809
DOI: 10.1055/s-0039-1690809
paper
Iodobenzene-Catalyzed Oxidative Cyclization for the Synthesis of Highly Functionalized Cyclopropanes
Financial support from the National Natural Science Foundation of China (21572033) and the Science and Technology Commission of Shanghai Municipality (19ZR1403400) is greatly appreciated.Further Information
Publication History
Received: 22 December 2019
Accepted after revision: 09 January 2020
Publication Date:
29 January 2020 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690809.
- Supporting Information
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