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Acetoxy Meldrum's Acid: A Versatile Acyl Anion Equivalent in the Pd-catalyzed Asymmetric Allylic Alkylation

Barry M Trost, Maksim Osipov, Philip S J Kaib, Mark T Sorum

Org Lett. 2011 Jun 17;13(12):3222-5.

PMID: 21615099

Abstract:

Acetoxy Meldrum's acid can serve as a versatile acyl anion equivalent in the Pd-catalyzed asymmetric allylic alkylation. The reaction of this nucleophile with various meso and racemic electrophiles afforded alkylated products in high yields and enantiopurities. These enantioenriched products are versatile intermediates that can be further functionalized using nitrogen- and oxygen-centered nucleophiles, affording versatile scaffolds for the synthesis of nucleoside analogues. These scaffolds were used to complete formal syntheses of the anti-HIV drugs carbovir, abacavir, and the antibiotic aristeromycin.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
CS3104402 Abacavir sulfate racemic Abacavir sulfate racemic Price
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