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Enantiospecific and Regioselective Rhodium-Catalyzed Allylic Alkylation:  Diastereoselective Approach to Quaternary Carbon Stereogenic Centers

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posted on 23.06.2000, 00:00 by P. Andrew Evans, Lawrence J. Kennedy
The enantiospecific and regioselective rhodium-catalyzed allylic alkylation of a series of chiral nonracemic allylic carbonates, followed by ozonolysis and reductive lactonization, provides a convenient route to optically active γ-lactones. Sequential alkylation and reductive alkylation furnished the α-quaternary-β-ternary substituted γ-lactone derivative as a ≥10:1 mixture of diastereoisomers.