Literature DB >> 36248610

Ring-Opening Carbonyl-Olefin Metathesis of Cyclobutenes.

Maxwell G Holl1, Tristan H Lambert1.   

Abstract

The ring-opening carbonyl-olefin metathesis of cyclobutenes to furnish γ,δ-unsaturated aldehydes-formal Claisen rearrangement products-is reported. The bistrifluoroacetic acid salt of 2,3-diazabicyclo[2.2.2]octane promotes these reactions efficiently with a variety of cyclobutenes and aldehydes, including aliphatic, α,β-unsaturated, aryl, and heteroaryl aldehydes. Catalytic reactions are also demonstrated.

Entities:  

Keywords:  carbonyl-olefin metathesis; cycloaddition; cyclobutenes; cycloreversion; hydrazine catalysis

Year:  2022        PMID： 36248610      PMCID： PMC9555816          DOI： 10.1021/acscatal.2c01188

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.700


  16 in total

Review 1.  Claisen rearrangement over the past nine decades.

Authors:  Ana M Martín Castro
Journal:  Chem Rev       Date:  2004-06       Impact factor: 60.622

2.  Organocatalytic carbonyl-olefin metathesis.

Authors:  Allison K Griffith; Christine M Vanos; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2012-11-05       Impact factor: 15.419

Review 3.  Recent advances in ruthenium-based olefin metathesis.

Authors:  O M Ogba; N C Warner; D J O'Leary; R H Grubbs
Journal:  Chem Soc Rev       Date:  2018-06-18       Impact factor: 54.564

4.  Enantioselective Synthesis of Cyclobutylboronates via a Copper-Catalyzed Desymmetrization Approach.

Authors:  Manuel Guisán-Ceinos; Alejandro Parra; Víctor Martín-Heras; Mariola Tortosa
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-09       Impact factor: 15.336

5.  GaCl3-Catalyzed Ring-Opening Carbonyl-Olefin Metathesis.

Authors:  Haley Albright; Hannah L Vonesh; Marc R Becker; Brandon W Alexander; Jacob R Ludwig; Ren A Wiscons; Corinna S Schindler
Journal:  Org Lett       Date:  2018-07-27       Impact factor: 6.005

6.  Metal-Free Ring-Opening Metathesis Polymerization with Hydrazonium Initiators.

Authors:  Phong K Quach; Jesse H Hsu; Ivan Keresztes; Brett P Fors; Tristan H Lambert
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-13       Impact factor: 16.823

7.  Iron(III)-catalysed carbonyl-olefin metathesis.

Authors:  Jacob R Ludwig; Paul M Zimmerman; Joseph B Gianino; Corinna S Schindler
Journal:  Nature       Date:  2016-04-27       Impact factor: 49.962

Review 8.  Carbonyl-Olefin Metathesis.

Authors:  Haley Albright; Ashlee J Davis; Jessica L Gomez-Lopez; Hannah L Vonesh; Phong K Quach; Tristan H Lambert; Corinna S Schindler
Journal:  Chem Rev       Date:  2021-06-16       Impact factor: 72.087

9.  Tropylium-promoted carbonyl-olefin metathesis reactions.

Authors:  Uyen P N Tran; Giulia Oss; Domenic P Pace; Junming Ho; Thanh V Nguyen
Journal:  Chem Sci       Date:  2018-05-04       Impact factor: 9.825

10.  Ring-opening carbonyl-olefin metathesis of norbornenes.

Authors:  Janis Jermaks; Phong K Quach; Zara M Seibel; Julien Pomarole; Tristan H Lambert
Journal:  Chem Sci       Date:  2020-07-01       Impact factor: 9.825
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