Iodotrimethylsilane-promoted additions of monoorganocopper compounds to. alpha.,. beta.-unsaturated ketones, esters, and lactones

M Bergdahl, M Eriksson, M Nilsson…

Index: Bergdahl, Mikael; Eriksson, Magnus; Nilsson, Martin; Olsson, Thomas Journal of Organic Chemistry, 1993 , vol. 58, # 25 p. 7238 - 7244

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Citation Number: 56

Abstract

Conjugate additions with the efficient monoorganocopper-iodotrimethylsilane combination, exemplified mainly with methylcopper, butylcopper, and tert-butylcopper, proceed cleanly, smoothly, and rapidly to a variety of a, B-unsaturated carbonyl compounds; cyclic and acyclic enones, 8-alkoxy enones, enoates and lactones in ether, THF, and dichloromethane, often at-78 OC. The RCu-(Li1)-TMSI reagent gives a good economy of group transfer with ...