Abstract
When lithium enolates generated from five chiral α, γ-disubstituted γ-lactones are treated with proton sources, formation of the α, γ-syn epimers always predominates over the a,y-anti epimers in ratios of 10.2–2.9:1. Higher syn/anti ratios are obtained via silyl enolates in some cases. Chirality discrimination by chiral proton source is also observed in particular cases.
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