Solvent-Catalyzed Ring-Chain-Ring Tautomerization in Axially Chiral Compounds

wim — Mon, 24 Oct 2011 08:55:17 +0000

A. Yıldırım, A. Konuklar, S. Catak, V. Van Speybroeck, M. Waroquier, I. Doğan, V. Aviyente

Chemistry - A European Journal

18 (40), 12725-12732

2012

Abstract

The mechanism of ring–chain–ring tautomerization and the prominent effect of the solvent environment have been computationally investigated in an effort to explain the enantiomeric interconversion observed in 2-oxazolidinone derivatives, heterocyclic analogues of biphenyl atropisomers, which were isolated as single stable enantiomers and have the potential to be used as axially chiral catalysts. This study has shed light on the identity of the intermediate species involved in the ring–chain–ring tautomerization process as well as the catalytic effect of polar protic solvents. These mechanistic details will prove very useful in predicting and understanding ring–chain tautomeric equilibria in similar heterocyclic systems and will further enable experimentalists to devise appropriate experimental conditions in which axially chiral catalysts remain stable as single enantiomers.

DOI

http://dx.doi.org/10.1002/chem.201200363

Private attachment

12_chem_eur_j_18(40)12725_Yildirim.pdf

Modeling Ring-chain-ring Tautomerization of N-(o-aryl)-4-Hydroxy-2-oxazolidinone Derivatives

wim — Mon, 17 Oct 2011 12:32:51 +0000

A. Yıldırım, A. Konuklar, S. Catak, V. Van Speybroeck, M. Waroquier, I. Doğan, V. Aviyente

Abstract PII 141

Poster

Conference / event / venue

Ninth Triennial Congress of the World Association of Theoretical and Computational Chemists (WATOC)

Santiago de Compostela, Spain

Sunday, 17 July, 2011 to Friday, 22 July, 2011

Abstract

WATOC2011-Asli Yildirim.pdf

Conference reference

WATOC 2011

Center for Molecular Modeling - A. Konuklar

Solvent-Catalyzed Ring-Chain-Ring Tautomerization in Axially Chiral Compounds

Abstract

DOI

Private attachment

Modeling Ring-chain-ring Tautomerization of N-(o-aryl)-4-Hydroxy-2-oxazolidinone Derivatives

Conference / event / venue

Abstract

Conference reference