1021452-58-3Relevant academic research and scientific papers
Synthesis of α-amino amides via N,O-acetals derived from Weinreb amides
Hirner, Sebastian,Somfai, Peter
supporting information; experimental part, p. 7798 - 7803 (2009/12/29)
(Chemical Equation Presented) An easy and straightforward synthesis of α-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 R-amino amides in excellent yields. Furthermore, a more generalized protocol for the α-arylation of Weinreb amides lacking an R-amino moiety is also discussed.
Synthesis of α-amino acids by umpolung of weinreb amide enolates
Hirner, Sebastian,Kirchner, Donata K.,Somfai, Peter
supporting information; experimental part, p. 5583 - 5589 (2009/05/11)
An efficient and diastereoselective synthesis of α-amino acids from readily available starting materials has been developed. The key feature of this reaction is an umpolung of a glycine-derived enolate, providing an alternative approach for the synthesis of α-amino acids. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Synthesis of aryl glycines by the α arylation of weinreb amides
Hirner, Sebastian,Panknin, Olaf,Edefuhr, Magnus,Somfai, Peter
, p. 1907 - 1909 (2008/12/22)
(Chemical Equation Presented) A rare example of the umpolung of an enolate forms the basis of the title reaction. In this procedure, a Grignard reagent is added to the iminium ion formed from the Weinreb amide upon treatment with a base (see scheme). When a chiral amide was used as the starting material, the nucleophilic addition proceeded with high diastereoselectivity. LDA = lithium diisopropylamide.
