Literature DB >> 14725473

Remarkable rate acceleration of imidazole-promoted Baylis-Hillman reaction involving cyclic enones in basic water solution.

Sanzhong Luo1, Peng George Wang, Jin-Pei Cheng.   

Abstract

The Baylis-Hillman reaction of cyclic enones was greatly accelerated in basic water solution with imidazoles as catalysts, which resulted in short reaction time, high yields, and expanding substrate scopes. Bicarbonate solution was shown to be the optimal reaction medium for the reaction in this study. The apparent "enhanced basicity" of imidazoles accounted for the rate increase in alkaline solution.

Entities:  

Year:  2004        PMID: 14725473     DOI: 10.1021/jo035345p

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  Amino acid ionic liquids as catalysts in a solvent-free Morita-Baylis-Hillman reaction.

Authors:  Mathias Prado Pereira; Rafaela de Souza Martins; Marcone Augusto Leal de Oliveira; Fernanda Irene Bombonato
Journal:  RSC Adv       Date:  2018-07-02       Impact factor: 4.036

2.  Engineering an efficient and enantioselective enzyme for the Morita-Baylis-Hillman reaction.

Authors:  Rebecca Crawshaw; Amy E Crossley; Linus Johannissen; Ashleigh J Burke; Sam Hay; Colin Levy; David Baker; Sarah L Lovelock; Anthony P Green
Journal:  Nat Chem       Date:  2021-12-16       Impact factor: 24.274

3.  Cracking the immune fingerprint of metal-organic frameworks.

Authors:  T Hidalgo; R Simón-Vázquez; A González-Fernández; P Horcajada
Journal:  Chem Sci       Date:  2021-11-05       Impact factor: 9.825

4.  Computational design of enone-binding proteins with catalytic activity for the Morita-Baylis-Hillman reaction.

Authors:  Sinisa Bjelic; Lucas G Nivón; Nihan Çelebi-Ölçüm; Gert Kiss; Carolyn F Rosewall; Helena M Lovick; Erica L Ingalls; Jasmine Lynn Gallaher; Jayaraman Seetharaman; Scott Lew; Gaetano Thomas Montelione; John Francis Hunt; Forrest Edwin Michael; K N Houk; David Baker
Journal:  ACS Chem Biol       Date:  2013-01-30       Impact factor: 5.100

5.  An Artificial Cofactor Catalyzing the Baylis-Hillman Reaction with Designed Streptavidin as Protein Host*.

Authors:  Horst Lechner; Vincent R Emann; M Breuning; Birte Höcker
Journal:  Chembiochem       Date:  2021-02-16       Impact factor: 3.164

  5 in total

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