Energy Barriers to Rotation in Axially Chiral Analogues of 4-(Dimethylamino)pyridine-Reference-Cited by-同舟云学术

Energy Barriers to Rotation in Axially Chiral Analogues of 4-(Dimethylamino)pyridine

Published:2001-10-10 Issue:22 Volume:66 Page:7394-7401
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Spivey Alan C.¹,Charbonneau Patrick¹,Fekner Tomasz¹,Hochmuth Detlev H.¹,Maddaford Adrian¹,Malardier-Jugroot Cecile¹,Redgrave Alison J.¹,Whitehead Michael A.¹

Affiliation:

1. Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, U.K., Theoretical Chemistry Laboratory, Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montreal, Quebec, Canada H3A 2K6, Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany, and GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, U.K.

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/jo015593q

Reference52 articles.

1. Enantiomerization refers to the reversible microscopic interconversion of enantiomers with a rate constantkenant. Racemization refers to the irreversible macroscopic conversion of an optically active mixture of enantiomers into or toward the racemate with a rate constantkracemwherekracem= 2kenantsince the interconversion of one molecule reduces the enantiomeric excess (ee) by two molecules. Dynamic HPLC studies and PM3, HF/STO-3G, and DFT/B3LYP/6-31G* calculations givekenantdirectly, whereas Eyring plots givekracemdirectly. Consequently, a statistical correction factor of 0.5 has been applied to the Eyring rate data to obtain correct kinetic parameters for enantiomerization (see Supporting Information).

2. Synthesis of atropisomeric analogues of DMAP

3. Configurationally Stable Biaryl Analogues of 4-(Dimethylamino)pyridine: A Novel Class of Chiral Nucleophilic Catalysts

4. ASYMMETRIC CATALYSIS OF ACYL TRANSFER BY LEWIS ACIDS AND NUCLEOPHILES. A REVIEW

Cited by 55 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Atroposelective Synthesis of Biaryl N‐Oxides via Cu‐Catalyzed De Novo Heteroaromatic N‐Oxide Ring Formation;Advanced Science;2024-08-09

2. Effective synthesis of menthol derivative monomenthyl succinate catalyzed by nanoscale silicon dioxide immobilized DMAP derivative in mixed solvent system;Comptes Rendus. Chimie;2020-11-10

3. Axial chirality in biaryl N , N ‐dialkylaminopyridine derivatives bearing an internal carboxy group;Chirality;2020-03-05

4. Synthesis of vitamin E succinate catalyzed by nano-SiO2 immobilized DMAP derivative in mixed solvent system;Green Processing and Synthesis;2019-01-28

5. Axially chiral tridentate isoquinoline derived ligands for diethylzinc addition to aldehydes;Tetrahedron;2018-09