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Organosilicon Reducing Reagents for Stereoselective Formations of Silyl Enol Ethers from α-Halo Carbonyl Compounds

Suman Pramanik, Supriya Rej, Shun Kando, Hayato Tsurugi* and Kazushi Mashima*

*Department of Chemistry, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka, 560-8531, Japan, Email: mashimachem.es.osaka-u.ac.jp, tsurugichem.es.osaka-u.ac.jp

S. Pramanik, S. Rej, S. Kando, H. Tsurugi, K. Mashima, J. Org. Chem., 2018, 83, 2395-2401.

DOI: 10.1021/acs.joc.7b03005 (free Supporting Information)


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Abstract

The use of 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine achieves a salt-free stereoselective synthesis of silyl enol ethers from α-halo carbonyl compounds. In this reaction, easily removable tetramethylpyrazine and trimethylsilyl halides were generated as byproducts. The inertness of the reaction byproducts enables one-pot transformations of the in situ generated silyl enol ethers into various α-functionalized carbonyls.


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Key Words

silyl enol ethers, trifuoromethylation


ID: J42-Y2018