54639-02-0Relevant articles and documents
Synthesis of α-Hydroxycarboxylic Acid Anilides via Copper-Catalyzed C-N Coupling of α-Hydroxyamides with Aryl Halides
Li, Zhijie,Wen, Quan,Zhou, Lihong,Deng, Xingmei,Zeng, Qingle
, p. 3751 - 3757 (2015/11/28)
The synthesis of highly important α-hydroxycarboxylic acid anilides via copper-catalyzed chemoselective C-N coupling reactions of α-hydroxyamides and aryl halides is described. This highly selective N-arylation process demonstrates wide substrate scope, c
Scope and Limitations of the TiCl4-Mediated Additions of Isocyanides to Aldehydes and Ketones with Formation of α-Hydroxycarboxylic Acid Amides
Seebach, Dieter,Adam, Geo,Gees, Thomas,Schiess, Martin,Weigand, Wolfgang
, p. 507 - 518 (2007/10/02)
The adducts obtained from TiCl4 and achiral (8-12) or chiral, nonracemic (13-22) isocyanides are combined with aldehydes (aromatic or aliphatic) and ketones (acetone, cyclohexanone, acetophenone) to give, after aqueous workup, α-hydroxyamides (27-55) .The transformation is compatible with a variety of functional groups (aromatic and heterocyclic rings, amino, ether, ester, and amido groups, halides, and phosphonate substituents).The yields range from 14 to over 95percent (with the lower values in the case of more highly functionalised isocyanides).No diastereoselectivity is observed with chiral isocyanides.If the R groups of the isocyanide (R-NC) form a rather stable cation (t-alkyl or benzylic), cyanohydrins may result from the reaction, rather than the N-substituted α-hydroxyamides (see Scheme 2).