A one-flask synthesis of Weinreb amides from chiral and achiral carboxylic acids using the deoxo-fluor fluorinating reagent.
[structure] The reagent [bis(2-methoxyethyl)amino]sulfur trifluoride (Deoxo-Fluor reagent) converts carboxylic acids to the corresponding acid fluorides, which then react with N,N-dimethylhydroxylamine to give the corresponding Weinreb amides in high yields. The reaction proceeds without racemization when optically active acids are used as the starting material. This method is operationally simple and provides the products in high purity.
Tunoori
A R
AR
Department of Medicinal Chemistry, Higuchi Biosciences Center, University of Kansas, Lawrence, Kansas 66045, USA.
White
J M
JM
Georg
G I
GI
D000577:Amides / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000737:chemistry*; D004123:Dimethylamines / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry
C419465:(bis(2-methoxyethyl)amino)sulfur trifluoride; D000577:Amides; D002264:Carboxylic Acids; D004123:Dimethylamines; D006845:Hydrocarbons, Fluorinated; D007202:Indicators and Reagents; D013457:Sulfur Compounds; C063231:N,N-dimethylhydroxylamine; D005459:Fluorides