2004
DOI: 10.1016/j.tetlet.2004.03.148
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Microwave-assisted cleavage of Weinreb amide for carboxylate protection in the synthesis of a ( R )-3-hydroxyalkanoic acid

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Cited by 24 publications
(19 citation statements)
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“…Hydrogenation of the double bond proceeded with simultaneous cleavage of the Obenzyl protecting group. Finally, the Weinreb amide was hydrolyzed with the assistance of microwave heating to give (R)-3-hydroxydecanoic acid (Scheme 28) [73].…”
Section: Chiral Pool-derived -Hydroxy Carboxylic Acids 121 From (S)mentioning
confidence: 99%
“…Hydrogenation of the double bond proceeded with simultaneous cleavage of the Obenzyl protecting group. Finally, the Weinreb amide was hydrolyzed with the assistance of microwave heating to give (R)-3-hydroxydecanoic acid (Scheme 28) [73].…”
Section: Chiral Pool-derived -Hydroxy Carboxylic Acids 121 From (S)mentioning
confidence: 99%
“…Palladium on charcoal-catalyzed transfer hydrogenation using ammonium formate is superior to catalytic hydrogenation for the removal of O-benzyl protecting groups as revealed from the synthesis of α-hydroxy-β-lactams (eq 9), 26 L-glycono-1,4-lactones, 27 (R)-3-hydroxyalkanoic acids, 28 and hydroxyindoles. 29 In the case of O-benzyl-protected monosaccharide derivatives (eq 10) 30 and O-benzyl-N-arylamidoximes (eq 11) 31 regioselective debenzylation is observed.…”
Section: First Updatementioning
confidence: 99%
“…Besides the characterization and quantitative description of the degradation of PHB, the proper control of the reaction also offers the possibility of producing (R)-3hydroxybutyric acid (3-HBA) in large purity. The production of 3-HBA is severely limited by the difficulties of chemical synthesis [83,84], in spite of the fact that the chiral compound is valuable biotechnologically and important in several application areas. It can be used for the synthesis of carbepenem antibiotics [85], as chiral building block for the production of macrolides (e.g.…”
Section: Introductionmentioning
confidence: 99%