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. 2000 Jul 27;2(15):2213-5.
doi: 10.1021/ol005953g.

Enantiospecific and regioselective rhodium-catalyzed allylic alkylation: diastereoselective approach to quaternary carbon stereogenic centers

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Enantiospecific and regioselective rhodium-catalyzed allylic alkylation: diastereoselective approach to quaternary carbon stereogenic centers

P A Evans et al. Org Lett. .

Abstract

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 gamma-lactones. Sequential alkylation and reductive alkylation furnished the alpha-quaternary-beta-ternary substituted gamma-lactone derivative as a >/=10:1 mixture of diastereoisomers.

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