Desymmetrization of meso-Anhydrides with Organozinc Reagents

Significance

Cross-coupling reactions are a powerful method to synthesize complex molecules. The use of cyclic meso-anhydrides as electrophiles for zinc nucleophiles in the presence of a chiral rhodium complex yield γ-keto acids with a stereodefined backbone. The authors use a variety of in situ generated organozinc reagents to obtain the products in >70% yield and >80% ee. Conversion into the core structure of eupomatilones can be achieved in three steps. See also previous work: J. Am. Chem. Soc. 2005, 127, 247; J. Am. Chem. Soc. 2004, 126, 10248.