http://www.cnr.it/ontology/cnr/individuo/prodotto/ID17777
An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent (Articolo in rivista)
- Type
- Label
- An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent (Articolo in rivista) (literal)
- Anno
- 2011-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1016/j.tet.2011.05.033 (literal)
- Alternative label
Pinna, Giovanni; Bellucci, Maria Cristina; Malpezzi, Luciana; Pisani, Laura; Superchi, Stefano; Volonterio, Alessandro; Zanda, Matteo (2011)
An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent
in Tetrahedron (Oxf., Print)
(literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Pinna, Giovanni; Bellucci, Maria Cristina; Malpezzi, Luciana; Pisani, Laura; Superchi, Stefano; Volonterio, Alessandro; Zanda, Matteo (literal)
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- ISI Web of Science (WoS) (literal)
- ISI Web of Science (WOS) (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
- Polytechnic University of Milan; University of Milan; University of Basilicata; CNR ICRM; University of Aberdeen (literal)
- Titolo
- An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent (literal)
- Abstract
- N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for alpha-hydroxy, alpha-chloro, and alpha-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective alpha-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under non-oxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail. (C) 2011 Elsevier Ltd. All rights reserved. (literal)
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