Enantioselective Synthesis of α-Alkyl-β,γ-unsaturated Esters through Efficient Cu-Catalyzed Allylic Alkylations
- 29 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (16) , 4690-4691
- https://doi.org/10.1021/ja0300618
Abstract
A method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and α,β-unsaturated carboxylic esters that bear a γ-phosphate is reported. These transformations afford α-alkyl-β,γ-unsaturated carbonyls with regioselectivities of 7:1 to >20:1 (SN2‘:SN2) and in 87−97% ee. The utility of the method is illustrated by a convergent total synthesis of topoisomerse II inhibitor (R)-elenic acid.Keywords
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