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

✍ Scribed by Mutsumi Sada; Dr. Taniyuki Furuyama; Dr. Shinsuke Komagawa; Prof. Dr. Masanobu Uchiyama; Prof. Dr. Seijiro Matsubara

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
358 KB
Volume
16
Category
Article
ISSN
0947-6539

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✦ Synopsis

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 CZn bond of the silyl enol ether could be used in a cross‐coupling reaction to form another CC 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.

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