Literature DB >> 21520959

N-Heterocyclic carbene (NHC)-catalyzed intermolecular hydroacylation of cyclopropenes.

Xavier Bugaut1, Fan Liu, Frank Glorius.   

Abstract

We report the first intermolecular NHC-catalyzed hydroacylation of electron-neutral olefins. Treatment of aromatic aldehydes with cyclopropenes under mild conditions affords valuable acylcyclopropanes in moderate to high yields with an excellent level of diastereocontrol. Preliminary mechanistic studies suggest that product formation occurs via a concerted syn hydroacylation pathway.
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID： 21520959     DOI： 10.1021/ja202594g

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  8 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

2.  Functionalized Cyclopropenes and Methylenecyclopropenes from Dianions of 3-Hydroxymethylcyclopropenes.

Authors:  Matthew D Hassink; Joseph M Fox
Journal:  Synthesis (Stuttg)       Date:  2012       Impact factor: 3.157

3.  Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors:  Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

4.  Facially selective Cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange.

Authors:  Vinod Tarwade; Ramajeyam Selvaraj; Joseph M Fox
Journal:  J Org Chem       Date:  2012-10-19       Impact factor: 4.354

5.  The effect of the N-mesityl group in NHC-catalyzed reactions.

Authors:  Jessada Mahatthananchai; Jeffrey W Bode
Journal:  Chem Sci       Date:  2012-01-01       Impact factor: 9.825

6.  Mechanistic insights into hydroacylation with non-chelating aldehydes†Electronic supplementary information (ESI) available: Materials and methods, reaction procedures, characterization data. CCDC 1012849. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4sc02026jClick here for additional data file.

Authors:  Stephen K Murphy; Achim Bruch; Vy M Dong
Journal:  Chem Sci       Date:  2014-09-22       Impact factor: 9.825

7.  Insights into the Competing Mechanisms and Origin of Enantioselectivity for N-Heterocyclic Carbene-Catalyzed Reaction of Aldehyde with Enamide.

Authors:  Yan Qiao; Xinhuan Chen; Donghui Wei; Junbiao Chang
Journal:  Sci Rep       Date:  2016-12-01       Impact factor: 4.379

8.  Regioselective hydroacylation of 1,3-dienes by cobalt catalysis.

Authors:  Qing-An Chen; Daniel K Kim; Vy M Dong
Journal:  J Am Chem Soc       Date:  2014-03-03       Impact factor: 15.419
  8 in total

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