Abstract
Functionalized secondary alkyllithium reagents obtained by I/Li exchange from the corresponding secondary alkyl iodides undergo two successive transmetalations with Me3 SiCH2 ZnBr⋅LiBr and CuBr⋅2 LiCl⋅Me2 S to provide functionalized secondary alkylcopper compounds with high retention of configuration. These alkylcopper derivatives react further with electrophiles such as alkynyl esters, acid chlorides, allylic chlorides, ketals, ethylene oxide, and 3-iodocyclopentanone with high retention of configuration. A related sequence of transmetalations with MeMgI and LaCl3 ⋅2 LiCl allows a retentive addition of secondary alkyllithium reagents to acetone. The influence of the solvent on the configurational stability of secondary alkylzinc reagents is described.
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