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Stereoselective Synthesis of Z-α,β-Unsaturated Sulfones Using Peterson Reagents. 2015

Kaori Ando, and Tomohiro Wada, and Miho Okumura, and Hiroshi Sumida
Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University , Yanagido 1-1, Gifu 501-1193, Japan.

New Peterson reagents were prepared by introducing alkyloxy groups on the silicon atom in order to fix the conformation of the sulfone anion. The reagents 1d and 1e reacted with a variety of aldehydes after the treatment with Li-base to give Z-α,β-unsaturated sulfones with up to >99:1 selectivity in good to excellent yields. For the reaction with aliphatic aldehydes, CPME (cyclopentyl methyl ether) is the choice of solvent, while DME (1,2-dimethoxyethane) gave higher selectivity for the reaction with aromatic aldehydes.

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