Catalytic Enantioselective Alkylation of Substituted Dioxanone Enol Ethers: Ready Access to C(α)‐Tetrasubstituted Hydroxyketones, Acids, and Esters
2008; Wiley; Volume: 47; Issue: 36 Linguagem: Inglês
10.1002/anie.200801424
ISSN1521-3773
AutoresMasaki Seto, Jennifer L. Roizen, Brian M. Stoltz,
Tópico(s)Asymmetric Hydrogenation and Catalysis
ResumoThe catalytic enantioselective formation of tetrasubstituted α-alkoxycarbonyl compounds is an ongoing challenge to synthetic chemists.[1]Fully-substituted α-hydroxyesters and acids comprise essential components of, and building blocks for, many bioactive natural products.These include quinic acid (1), cytotoxic leiodolide A (2),[2] and the anti-cancer agents in the harringtonine series (3a-f), whose activities depend dramatically on the presence and composition of an α-hydroxyester side-chain.[3]While many approaches to these important moieties exist, [4,5] we envisioned applying our recently developed palladium-catalyzed methods for the formation of enantioenriched all-carbon quaternary stereocenters in cyclic alkanones[6] to a general synthesis of C(α)-tetrasubstituted hydroxy carbonyl compounds.[7]
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