Synthesis of alpha-amino amides via N,O-acetals derived from Weinreb amides.
An easy and straightforward synthesis of alpha-amino amides via a base-mediated rearrangement of modified Weinreb amides into N,O-acetals is presented. Subsequent arylation, alkylation, alkenylation, or alkynylation of this intermediate affords the corresponding alpha-amino amides in excellent yields. Furthermore, a more generalized protocol for the alpha-arylation of Weinreb amides lacking an alpha-amino moiety is also discussed.
Hirner
Sebastian
S
Organic Chemistry, KTH Chemical Science and Engineering, SE-100 44 Stockholm, Sweden.
Somfai
Peter
P
D000080:Acetals / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*
D000080:Acetals; D000577:Amides; D009584:Nitrogen; D010100:Oxygen