In addition to organic halides, alkyl tosylates (R'OTs, Section 9.13) also react with organocuprates ( ${\mathbf{R}}_{\mathbf{2}}\mathbf{CuLi}$) to form coupling products R-R'. When 2° alkyl tosylates are used as starting materials ( ${\mathbf{R}}_{\mathbf{2}}\mathbf{CHOTs}$), inversion of the configuration at a stereogenic center results. Keeping this in mind, draw the product formed when each compound is treated with ${\mathbf{\left(}{\mathbf{CH}}_{\mathbf{3}}\mathbf{\right)}}_{\mathbf{2}}\mathbf{CuLi}$.

a.

b.

The incorporation of tosyl chloride into alkyl alcohols leads to the formation of alkyl tosylates. Tosyl groups serve as protecting groups in the area of organic chemistry.

The combination of alkyl tosylate with an organocuprate reagent results in the generation of a product possessing new C-C bonds.

The species comprising copper-carbon bonds are termed organocuprate reagents. These reagents function as nucleophiles and combine with alkyl tosylate to form coupling products and comprise a new C-C bond.

a. The reaction of compound a with organocuprates can be given as follows.

Reaction of compound a with organocuprates

b. The reaction of compound b with organocuprates can be given as follows.

Reaction of compound b with organocuprates