Chemoselective Synthesis of N‐Substituted α‐Amino‐α′‐chloro Ketones via Chloromethylation of Glycine‐Derived Weinreb Amides
Identifieur interne : 000695 ( Main/Exploration ); précédent : 000694; suivant : 000696Chemoselective Synthesis of N‐Substituted α‐Amino‐α′‐chloro Ketones via Chloromethylation of Glycine‐Derived Weinreb Amides
Auteurs : Vittorio Pace [Espagne] ; Wolfgang Holzer ; Guido Verniest [Belgique] ; Andrés R. Alcántara [Espagne] ; Norbert De Impe [Belgique]Source :
- Advanced Synthesis & Catalysis [ 1615-4150 ] ; 2013-03-25.
English descriptors
- KwdEn :
- Amide, Angew, Bioactive compounds, Carbonyl, Carbonyl group, Catal, Chem, Chemoselective synthesis, Chloro, Chloro ketone, Chloromethylation, Chloromethylation reaction, Chloromethyllithium, Clch2i, Derivative, Ester, Glycine, Gmbh, Green chem, Homologation, Izawa, Ketone, Kgaa, Lett, Nitrogen atom, Other hand, Reaction temperature, Synth, Tetrahedron, Tetrahedron lett, Verlag, Verlag gmbh, Vittorio pace, Weinheim, Weinreb, Weinreb amide, Weinreb amides.
- Teeft :
- Amide, Angew, Bioactive compounds, Carbonyl, Carbonyl group, Catal, Chem, Chemoselective synthesis, Chloro, Chloro ketone, Chloromethylation, Chloromethylation reaction, Chloromethyllithium, Clch2i, Derivative, Ester, Glycine, Gmbh, Green chem, Homologation, Izawa, Ketone, Kgaa, Lett, Nitrogen atom, Other hand, Reaction temperature, Synth, Tetrahedron, Tetrahedron lett, Verlag, Verlag gmbh, Vittorio pace, Weinheim, Weinreb, Weinreb amide, Weinreb amides.
Abstract
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.
Url:
DOI: 10.1002/adsc.201201043
Affiliations:
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Alcántara</name><affiliation wicri:level="2"><country xml:lang="fr">Espagne</country><wicri:regionArea>Department of Organic and Pharmaceutical Chemistry, Complutense University of Madrid, Pza. 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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.</div></front></TEI><affiliations><list><country><li>Belgique</li><li>Espagne</li></country><region><li>Communauté de Madrid</li></region></list><tree><noCountry><name sortKey="Holzer, Wolfgang" sort="Holzer, Wolfgang" uniqKey="Holzer W" first="Wolfgang" last="Holzer">Wolfgang Holzer</name></noCountry><country name="Espagne"><region name="Communauté de Madrid"><name sortKey="Pace, Vittorio" sort="Pace, Vittorio" uniqKey="Pace V" first="Vittorio" last="Pace">Vittorio Pace</name></region><name sortKey="Alcantara, Andres R" sort="Alcantara, Andres R" uniqKey="Alcantara A" first="Andrés R." last="Alcántara">Andrés R. Alcántara</name><name sortKey="Pace, Vittorio" sort="Pace, Vittorio" uniqKey="Pace V" first="Vittorio" last="Pace">Vittorio Pace</name></country><country name="Belgique"><noRegion><name sortKey="Verniest, Guido" sort="Verniest, Guido" uniqKey="Verniest G" first="Guido" last="Verniest">Guido Verniest</name></noRegion><name sortKey="De Impe, Norbert" sort="De Impe, Norbert" uniqKey="De Impe N" first="Norbert" last="De Impe">Norbert De Impe</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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