Premium
Stereoselective Control by Face‐to‐Face Versus Edge‐to‐Face Aromatic Interactions: The Case of C 3 ‐Ti IV Amino Trialkolate Sulfoxidation Catalysts
Author(s) -
Santoni Gabriella,
Mba Miriam,
Bonchio Marcella,
Nugent William A.,
Zonta Cristiano,
Licini Giulia
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902072
Subject(s) - stereoselectivity , enantiopure drug , steric effects , chemistry , enantiomer , catalysis , aromaticity , stereochemistry , organic chemistry , enantioselective synthesis , molecule
The stereoselective oxidation of differently functionalised benzyl phenyl sulfides has been examined by using enantiopure Ti IV trialkanolamine complexes. These complexes efficiently catalyse the sulfoxidation with good stereoselectivities. The data highlight the contribution to the stereoselectivity of steric effects and non‐covalent π–π interactions between the aromatic rings of the Ti IV complex and those pertaining to the substrates. Enantiomeric excesses have been correlated with the electrostatic potential surfaces (EPS) of the reacting sulfides. The overall study leads to a mechanistic interpretation that explains the stereoselectivity of the system and dissects the role of aromatic and steric interactions in the stereoselective process.