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http://dx.doi.org/10.5012/bkcs.2010.31.10.2776

A New Synthesis of Triphenylphosphorane Ylide Precursors to α-Keto Amide/Ester and Tricarbonyl Units via Horner-Wadsworth-Emmons Reaction  

Lee, Kie-Seung (Department of Applied Chemistry, Woosuk University)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.10, 2010 , pp. 2776-2782 More about this Journal
Abstract
Newly developed Horner-Wadsworth-Emmons (HWE) reagents 5 having triphenylphosphorane ylide subunits readily condensed with various carbonyl compounds under mild reaction conditions to afford $\beta,\gamma$-unsaturated $\alpha$-keto triphenylphorane ylides in good to excellent yields, which were hydrogenated over Pd-C (10%)/$H_2$ (1 atm) to give the corresponding $\alpha$-keto triphenylphorane ylides in quasi-quantitative yields. These triphenyphosphorane ylides have been utilized as the precursors to $\alpha$-keto amide/ester and vicinal tricarbonyl units in Wasserman's synthetic protocols, and have previously been prepared only from carboxylic acids/acid chlorides. Our new approaches provide excellent alternatives for the synthesis of triphenylphosphorane ylide precursors to $\alpha$-keto amide/ester and vicinal tricarbonyl units directly from carbonyl compounds in good to excellent yields.
Keywords
$\alpha$-Keto amide; $\alpha$-Keto ester; Vicinal tricarbonyl; Triphenylphosphorane ylide; Horner-Wadsworth-Emmons reaction;
Citations & Related Records
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