Stereoselective Synthesis of Z-α,β-Unsaturated Sulfones Using Peterson Reagents
- 4 December 2015
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 17 (24), 6026-6029
- https://doi.org/10.1021/acs.orglett.5b03008
Abstract
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.Keywords
Funding Information
- Ministry of Education, Culture, Sports, Science, and Technology
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