Literature DB >> 16446807

Michael reactions carried out using a bench-top flow system.

Frederic Bonfils1, Isabelle Cazaux, Philip Hodge, Claude Caze.   

Abstract

The Michael reaction between methyl 1-oxoindan-2-carboxylate and methyl vinyl ketone was achieved successfully by pumping solutions of the reactants in toluene through a fluid bed of Amberlyst A21 at 50 degrees C. The use of a fluid bed reactor is attractive as it allows gel-type beads, i.e. the type of bead used in most studies of polymer-supported (PS) organic reactions, to be used satisfactorily in a flow system. When polymer-supported cinchonidine was used in place of Amberlyst A21, the Michael product was obtained in high yield with an enantiomeric excess (ee) of 51%. This % ee is comparable to that achieved when the reaction was catalysed by cinchonidine itself.

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Year:  2005        PMID: 16446807     DOI: 10.1039/b515241k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  6 in total

1.  The flow synthesis of heterocycles for natural product and medicinal chemistry applications.

Authors:  Marcus Baumann; Ian R Baxendale; Steven V Ley
Journal:  Mol Divers       Date:  2010-10-20       Impact factor: 2.943

2.  Continuous flow based catch and release protocol for the synthesis of alpha-ketoesters.

Authors:  Alessandro Palmieri; Steven V Ley; Anastasios Polyzos; Mark Ladlow; Ian R Baxendale
Journal:  Beilstein J Org Chem       Date:  2009-05-20       Impact factor: 2.883

3.  Continuous flow enantioselective arylation of aldehydes with ArZnEt using triarylboroxins as the ultimate source of aryl groups.

Authors:  Julien Rolland; Xacobe C Cambeiro; Carles Rodríguez-Escrich; Miquel A Pericàs
Journal:  Beilstein J Org Chem       Date:  2009-10-15       Impact factor: 2.883

4.  Nanofiltration-Enabled In Situ Solvent and Reagent Recycle for Sustainable Continuous-Flow Synthesis.

Authors:  Tamas Fodi; Christos Didaskalou; Jozsef Kupai; Gyorgy T Balogh; Peter Huszthy; Gyorgy Szekely
Journal:  ChemSusChem       Date:  2017-08-16       Impact factor: 8.928

5.  Synthesis of unsymmetrically substituted biaryls via sequential lithiation of dibromobiaryls using integrated microflow systems.

Authors:  Aiichiro Nagaki; Naofumi Takabayashi; Yutaka Tomida; Jun-ichi Yoshida
Journal:  Beilstein J Org Chem       Date:  2009-04-29       Impact factor: 2.883

6.  Asymmetric reactions in continuous flow.

Authors:  Xiao Yin Mak; Paola Laurino; Peter H Seeberger
Journal:  Beilstein J Org Chem       Date:  2009-04-29       Impact factor: 2.883

  6 in total

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