Literature DB >> 17867693

Enol esters: versatile substrates for Mannich-type multicomponent reactions.

Nicolas Isambert1, Montse Cruz, María José Arévalo, Elena Gómez, Rodolfo Lavilla.   

Abstract

The interaction of cyclic enol esters with diversely substituted anilines and ethyl glyoxalate yields, under Sc(OTf)3 catalysis, disubstituted N-aryl lactams in a multicomponent reaction. The protocol allows access to the trans stereoisomers after an epimerization of the initial mixture in which the cis isomers predominate. Vinyl acetate yields quinoline derivatives, whereas isopropenyl acetate leads to the corresponding Mannich adducts.

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Year:  2007        PMID: 17867693     DOI: 10.1021/ol701717z

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


  7 in total

1.  Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.

Authors:  Barbara J Casavant; Zainab M Khoder; Ilyas A Berhane; Sherry R Chemler
Journal:  Org Lett       Date:  2015-12-01       Impact factor: 6.005

2.  Scope and Mechanistic Investigations on the Solvent-Controlled Regio- and Stereoselective Formation of Enol Esters from the Ruthenium-Catalyzed Coupling Reaction of Terminal Alkynes and Carboxylic Acids.

Authors:  Chae S Yi; Ruili Gao
Journal:  Organometallics       Date:  2009-10-30       Impact factor: 3.876

3.  Catalytic Enantioselective Hydrovinylation of Trialkylsilyloxy and Acetoxy-1,3-Dienes: Cationic Co(I) Complexes for the Synthesis of Chiral Enolate Surrogates and Their Applications for Synthesis of Ketones and Cross-Coupling Reagents in High Enantiomeric Purity.

Authors:  Souvagya Biswas; Kendra R Dewese; Balaram Raya; T V RajanBabu
Journal:  ACS Catal       Date:  2022-04-14       Impact factor: 13.700

4.  Interplay between the Directing Group and Multifunctional Acetate Ligand in Pd-Catalyzed anti-Acetoxylation of Unsymmetrical Dialkyl-Substituted Alkynes.

Authors:  Javier Corpas; Enrique M Arpa; Romain Lapierre; Inés Corral; Pablo Mauleón; Ramón Gómez Arrayás; Juan C Carretero
Journal:  ACS Catal       Date:  2022-05-19       Impact factor: 13.700

Review 5.  Multicomponent Reactions for the Synthesis of Active Pharmaceutical Ingredients.

Authors:  Ángel Cores; José Clerigué; Emmanuel Orocio-Rodríguez; J Carlos Menéndez
Journal:  Pharmaceuticals (Basel)       Date:  2022-08-17

Review 6.  Recent advances in the chemistry of imine-based multicomponent reactions (MCRs).

Authors:  Lokman H Choudhury; Tasneem Parvin
Journal:  Tetrahedron       Date:  2011-07-18       Impact factor: 2.457

7.  Phosphine-Free Ru-Catalyzed Regio- and Stereoselective Addition of Benzoic Acids to Trifluoromethylated Alkynes toward Facile Access to Trifluoromethyl Group-Substituted (E)-Enol Esters.

Authors:  Guangyuan Liu; Xingxing Zhang; Guanghua Kuang; Naihao Lu; Yang Fu; Yiyuan Peng; Qiang Xiao; Yirong Zhou
Journal:  ACS Omega       Date:  2020-02-20
  7 in total

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