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3.5.2 Reactions with Acid Chlorides

Acid chlorides react with organocopper reagents to give ketones (Scheme 5).

Scheme 5

 

3.5.3 Conjugate Addition

Organocopper reagents undergo 1,4-addition to α,β -unsaturated carbonyl compounds. The reaction can be stereoselective. For example, the less substituted double bond undergoes reaction from the less hindered side to give stereoselective product (Scheme 6).

Scheme 6

Mechanism

The reaction takes place via copper(III) intermediate (Scheme 7).

Scheme 7

3.5.4 Reactions with Aldehydes and Ketones

Aldehydes readily react with organocuprates to give alcohols (Scheme 8). However, ketones are less reactive, but their reactivity can be accelerated using chlorotrimethylsilane.

Scheme 8