Abstract
Publisher Summary This chapter discusses chemistry of organocopper reagents such as alkylcopper reagents, allylcopper reagents, vinylcopper reagents,and mixed cuprate (I) reagents. The most significant and recent contribution to the understanding of conjugate additions of dialkyl cuprates to enones comes from House's correlation of enone-reduction potentials with 1, 4-additions. As a qualitative rule, unsaturated esters and ketones, which have reduction potentials lying in the range of minus 1.64 up to 2.3 volts, react rapidly with lithium dimethylcuprate to form conjugate addition products. The vinylcuprate is prepared from the corresponding lithium species, which in turn are obtained by metallation of the trans-vinyl iodide. The conjugate addition is highly stereospecific and yields diastereomeric trans-isomers. Further, some of the practical limitations of various organocuprate reagents include the use of thermally unstable sec- and tert- alkyl cuprates and the need for a large excess of copper reagent to obtain high conversions. The advent of using inert ligands as part of the mixed cuprates enhances the stability of the cuprates in some cases and maximizes the efficiency of transferring desired organic ligands.
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