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Effect of aggregation on stereochemistry and mechanism of asymmetric oxidation of the lithium enolate of methyl 3,3-dimethylbutanoate in the solid state and in solution
Journal article   Peer reviewed

Effect of aggregation on stereochemistry and mechanism of asymmetric oxidation of the lithium enolate of methyl 3,3-dimethylbutanoate in the solid state and in solution

Wei Yen, R. Bakthavatchalam, Jin Xian-Ming, Christopher K. Murphy and Franklin A. Davis
Tetrahedron letters, v 34(23), pp 3715-3718
1993

Abstract

Oxidation of the title enolate by enantiopure (camphorylsulfonyl)oxaziridines in THF afforded α-hydroxyester with 53–73% ee, but the product from the solid state reactions was racemic. The results suggest that the enolate exists and reacts as an aggregate in the solid state reactions. Oxidation of 1 by enantiopure 2 in THF afforded enantioenriched 3 with 53–73% ee, but 3 from the solid state reactions was recemic. The results suggest that the enolate exists and reacts as an aggregate in the solid state reactions.

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Web of Science research areas
Chemistry, Organic
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