Chemoselective Synthesis of N‐Substituted α‐Amino‐α′‐chloro Ketones via Chloromethylation of Glycine‐Derived Weinreb Amides. Issue 5 (28th February 2013)

• Record Type: Journal Article
• Authors: Pace, Vittorio; Holzer, Wolfgang; Verniest, Guido; Alcántara, Andrés R.; De Kimpe, Norbert
• Is Part Of: Advanced synthesis & catalysis. Volume 355:Issue 5(2013)
• Page Start: 919
• Page End: 926
• Publication Date: 2013-02-28
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201201043
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Functionalized α‐arylamino‐α′‐chloro ketones are obtained in high yield <italic>via</italic> a straightforward homologation reaction of Weinreb amides derived from <italic>N</italic>‐arylglycines using <italic>in situ</italic> generated chloromethyllithium. The use of the Weinreb amides is essential and allows the chemoselective homologation of <italic>N</italic>‐aryl‐<italic>N</italic>‐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.</p> </abstract>