Literature DB >> 11975646

Metal-promoted variants of the Passerini reaction leading to functionalized heterocycles.

Qian Xia1, Bruce Ganem.   

Abstract

[reaction: see text]. The effect of replacing the Brønsted acid in classic Passerini reactions with a mild Lewis acid has been studied. Triggered by metal-promoted silylation, condensations of aliphatic or aromatic carbonyl compounds with appropriately substituted isonitriles capable of neighboring group donation afford alpha-hydroxyamides, substituted oxazoles, and other useful heterocycles.

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Year:  2002        PMID： 11975646     DOI： 10.1021/ol025877c

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

Review 1.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

2.  Strategies for innovation in multicomponent reaction design.

Authors:  Bruce Ganem
Journal:  Acc Chem Res       Date:  2009-03-17       Impact factor: 22.384

3.  Hexafluoroisopropanol as the Acid Component in the Passerini Reaction: One-Pot Access to β-Amino Alcohols.

Authors:  Jordy M Saya; Rayan Berabez; Pim Broersen; Imme Schuringa; Art Kruithof; Romano V A Orru; Eelco Ruijter
Journal:  Org Lett       Date:  2018-06-15       Impact factor: 6.005
  3 in total

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