Stereoselective Sequential Spirocyclopropanation/Cloke–Wilson Rearrangement Reactions for Synthesis of trans-β,γ-Disubstituted γ‑Butyrolactones Using Alkylidene Meldrum’s Acid and Benzyl Halides
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The stereoselective sequential spirocyclopropanation/Cloke–Wilson rearrangement reactions have been developed to synthesize γ-butyrolactones using alkylidene Meldrum’s acids and benzyl halides. The DBU-promoted spirocyclopropanation was carried out efficiently at room temperature to generate trans-isomeric spirocyclopropyl Meldrum’s acid, and the following stereospecific thermal decarboxylative Cloke–Wilson rearrangement afforded trans-γ-butyrolactones. A variety of aromatic and aliphatic Meldrum’s acid derived olefins and benzyl halides were tolerated. Various trans-β,γ-disubstituted γ-butyrolactones were produced with moderate to good overall yields from 46 to 96% and excellent diastereoselectivities.
创建时间：
2020-01-10
