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Stereoselective Synthesis of Z-α,β-Unsaturated Sulfones Using Peterson Reagents

Kaori Ando*, Tomohiro Wada, Miho Okumura and Hiroshi Sumida

*Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan, Email: andogifu-u.ac.jp

K. Ando, T. Wada, M. Okumura, H. Sumida, Org. Lett., 2015, 17, 6026-6029.

DOI: 10.1021/acs.orglett.5b03008 (free Supporting Information)


Abstract

Peterson reagents, in which alkyloxy groups on the silicon atom fix the conformation of the anion after treatment with Li-base, were reacted with a variety of aldehydes to give Z-α,β-unsaturated sulfones with high Z-selectivity in very good yields. For the reaction with aliphatic aldehydes, cyclopentyl methyl ether is the solvent of choice, while 1,2-dimethoxyethane gave higher selectivity for the reaction with aromatic aldehydes.

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Key Words

vinyl sulfones, Z-alkenes, Peterson Olefination


ID: J54-Y2015