NDLI: 1,4-Addition of Bis(iodozincio)methane to α,β-Unsaturated Ketones: Chemical and Theoretical/Computational Studies

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Furuyama, Taniyuki Komagawa, Shinsuke Sada, Mutsumi Uchiyama, Masanobu Matsubara, Seijiro
Description	Author Affiliation: Sada M ( Department of Material Chemistry, Graduate School of Engineering, Kyoudai-katsura, Nishikyo, Kyoto 615-8510, Japan.)
Abstract	1,4-Addition of bis(iodozincio)methane to simple α,β-unsaturated ketones does not proceed well; the reaction is slightly endothermic according to DFT calculations. In the presence of chlorotrimethylsilane, the reaction proceeded efficiently to afford a silyl enol ether of β-zinciomethyl ketone. The CZn bond of the silyl enol ether could be used in a cross-coupling reaction to form another CC bond in a one-pot reaction. In contrast, 1,4-addition of the dizinc reagent to enones carrying an acyloxy group proceeded very efficiently without any additive. In this case, the product was a 1,3-diketone, which was generated in a novel tandem reaction. A theoretical/computational study indicates that the whole reaction pathway is exothermic, and that two zinc atoms of bis(iodozincio)methane accelerate each step cooperatively as effective Lewis acids.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	34
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-09-10
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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1,4-Addition of Bis(iodozincio)methane to α,β-Unsaturated Ketones: Chemical and Theoretical/Computational Studies