1260085-90-2Relevant academic research and scientific papers
Chemoselective synthesis of N-substituted α-amino-α′- chloro ketones via chloromethylation of glycine-derived Weinreb amides
Pace, Vittorio,Holzer, Wolfgang,Verniest, Guido,Alcantara, Andres R.,De Kimpe, Norbert
supporting information, p. 919 - 926 (2013/05/08)
Functionalized α-arylamino-α′-chloro ketones are obtained in high yield via a straightforward homologation reaction of Weinreb amides derived from N-arylglycines using in situ generated chloromethyllithium. The use of the Weinreb amides is essential and allows the chemoselective homologation of N-aryl-N-substituted glycine analogues, a transformation which is not possible using similar glycine esters. The procedure is promising for the large-scale preparation of α-amino-α′-chloropropanones, which are valuable precursors for a variety of bioactive compounds. Copyright
First general route to substituted α-arylamino-α′ chloropropan-2-ones by oxidation of N-protected aminohalohydrins: The importance of disrupting hydrogen bond networks
Pace, Vittorio,Cabrera, Alvaro Cortes,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.
experimental part, p. 3545 - 3555 (2010/12/19)
The presence of a network of intra- and intermolecular hydrogen bonds in β-arylamino alcohols, confirmed by both IR spectroscopy and computer modeling, inhibits their oxidation to the corresponding α-amino ketones. A straightforward protocol, including highly regioselective protection (as carbamates) and subsequent oxidation with Dess-Martin periodinane, affords near quantitative yields of the desired N-protected ketones, which upon mild treatment with iodotrimethylsilane leads to a series of differently functionalized α-arylamino-α′-chloro ketones. Georg Thieme Verlag Stuttgart.
