Literature DB >> 27549614

Annulation of o-Quinodimethanes through N-Heterocyclic Carbene Catalysis for the Synthesis of 1-Isochromanones.

Daniel Janssen-Müller1, Santanu Singha1, Theresa Olyschläger1, Constantin G Daniliuc1, Frank Glorius1.   

Abstract

The activation of 2-(bromomethyl)benzaldehydes using N-heterocyclic carbenes represents a novel approach to the generation of o-quinodimethane (o-QDM) intermediates. Coupling with ketones such as phenylglyoxylates, isatins, or trifluoromethyl ketones via [4 + 2] annulation gives access to functionalized 1-isochromanones.

Entities:  

Year:  2016        PMID： 27549614     DOI： 10.1021/acs.orglett.6b02335

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


  4 in total

1.  Carbene-Catalyzed Enantioselective Decarboxylative Annulations to Access Dihydrobenzoxazinones and Quinolones.

Authors:  Ansoo Lee; Joshua L Zhu; Taisiia Feoktistova; Alexander C Brueckner; Paul H-Y Cheong; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-27       Impact factor: 15.336

2.  N-Heterocyclic Carbene and Chiral Brønsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.

Authors:  Dian-Feng Chen; Tomislav Rovis
Journal:  Synthesis (Stuttg)       Date:  2016-11-18       Impact factor: 3.157

3.  Thermal Hetero-Diels-Alder Reaction of Benzocyclobutenones with Isatins To Form 2-Oxindole Spirolactones.

Authors:  Thomas Wurm; Ben W H Turnbull; Brett R Ambler; Michael J Krische
Journal:  J Org Chem       Date:  2017-11-22       Impact factor: 4.354

4.  N-Heterocyclic Carbene Catalyzed Photoenolization/Diels-Alder Reaction of Acid Fluorides.

Authors:  Andreas Mavroskoufis; Keerthana Rajes; Paul Golz; Arush Agrawal; Vincent Ruß; Jan P Götze; Matthew N Hopkinson
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-09       Impact factor: 15.336
  4 in total

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