Literature DB >> 12530884

Origins of boat or chair preferences in the Ireland-Claisen rearrangements of cyclohexenyl esters: a theoretical study.

Mahmood M Khaledy1, Mohammad Y S Kalani, Kelli S Khuong, K N Houk, Viktorya Aviyente, Reinhard Neier, Nicolas Soldermann, Joerg Velker.   

Abstract

The relative energies of the chair and boat transition states of a variety of Ireland-Claisen rearrangements were obtained by B3LYP/6-31G calculations. Theoretical results are in good agreement with experimental data and provide a quantitative analysis of the origins of boat preferences that are observed in some of these reactions.

Entities:  

Mesh：

Substances：

Year:  2003        PMID： 12530884     DOI： 10.1021/jo020595b

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


  7 in total

1.  A density functional theory approach toward substituent effect in Meerwein-Eschenmoser-Claisen rearrangement.

Authors:  Rahim Ghadari; Ahmad Shaabani
Journal:  J Mol Model       Date:  2011-04-27       Impact factor: 1.810

2.  Computational study of factors controlling the boat and chair transition states of Ireland-Claisen rearrangements.

Authors:  Seref Gül; Franziska Schoenebeck; Viktorya Aviyente; K N Houk
Journal:  J Org Chem       Date:  2010-03-19       Impact factor: 4.354

3.  Practical Organocatalytic Synthesis of Functionalized Non-C2-Symmetrical Atropisomeric Biaryls.

Authors:  Hongyin Gao; Qing-Long Xu; Craig Keene; Muhammed Yousufuddin; Daniel H Ess; László Kürti
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-23       Impact factor: 15.336

4.  A Computational Study of the Origin of Stereoinduction in NHC-Catalyzed Annulation Reactions of α,β-Unsaturated Acyl Azoliums.

Authors:  Eirik Lyngvi; Jeffrey W Bode; Franziska Schoenebeck
Journal:  Chem Sci       Date:  2012-03-01       Impact factor: 9.825

5.  Global Diastereoconvergence in the Ireland-Claisen Rearrangement of Isomeric Enolates: Synthesis of Tetrasubstituted α-Amino Acids.

Authors:  Tyler J Fulton; Alexander Q Cusumano; Eric J Alexy; Yun E Du; Haiming Zhang; K N Houk; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2020-12-15       Impact factor: 15.419

6.  Concise Total Synthesis of Lundurines A-C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization.

Authors:  Mariia S Kirillova; Michael E Muratore; Ruth Dorel; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2016-03-15       Impact factor: 15.419

7.  Formal Total Synthesis of Salvinorin A.

Authors:  Marc Halang; Martin E Maier
Journal:  ChemistryOpen       Date:  2022-02-26       Impact factor: 2.630
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.