Construction of Polycyclic β-Ketoesters Using a Homoconjugate Addition/Decarboxylative Dieckmann Annulation Strategy

Zhiwei Chen, Allen Y. Hong* and Xin Linghu

*Department of Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States, Email: hong.allengene.com

Z. Chen, A. Y. Hong, X. Linhu, J. Org. Chem., 2018, 83, 6225-6234.

DOI: 10.1021/acs.joc.8b00754

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Abstract

A CuI·SMe₂-mediated homoconjugate addition followed by a decarboxylative Dieckmann cyclization provides arene-fused cyclic β-ketoesters from 2-iodoaryl esters and 1,1-cyclopropane diesters. Various iodoaryl esters and 1,1-cyclopropane diesters were evaluated, and the limitations of both reactions are discussed.

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Key Words

Tetralones, Dieckmann Condensation

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ID: J42-Y2018