A short strategy for the synthesis of dimeric <i>trans</i>-2,3-disubstituted γ–butyrolactones from simple esters is described. This three-step process uses the diastereoselectivity of titanium enolate homocoupling chemistry to dimerize and set the trans stereochemistry in very high selectivity in the molecules described. The resulting diesters are converted to 1,4-diols which are then lactonized by a one-pot selective oxidation-lactonization sequence to give the desired γ–butyrolactones. The method is used in the synthesis of various 2,3-diaryl and dialkyl γ–butyrolactones.

Diastereoselective synthesis of <i>trans</i>-2,3-disubstituted γ–butyrolactones

Macromolecular Chemistry: The Second Century

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Diastereoselective synthesis of trans-2,3-disubstituted γ–butyrolactones