Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids
Naoyuki Shimada, Naoya Takahashi, Naoki Ohse, Masayoshi Koshizuka, Kazuishi Makino
Abstract
The first successful example of the direct synthesis of Weinreb amides using catalytic hydroxy-directed dehydrative amidation of carboxylic acids using the diboronic acid anhydride catalyst is described. The methodology is applicable to the concise syntheses of eight α-hydroxyketone natural products, namely, sattabacin, 4-hydroxy sattabacin, kurasoins A and B, soraphinols A and B, and circumcins B and C.
Topics & Concepts
CatalysisChemistryCarboxylic acidAcid anhydrideOrganic chemistryCombinatorial chemistryEpoxyChemical Synthesis and AnalysisAdvanced Synthetic Organic ChemistrySynthetic Organic Chemistry Methods