Novel chiral indole ligands for catalytic asymmetric allylic substitutions

Chirality is a fundamental property of three-dimensional objects. A chiral molecule is the one that is not superimposable with its mirror image. Chiral compounds are extremely important in pharmaceutical industry. Most isomers with chirality exhibit different biological activities such as pharmacology, toxicology, pharmacokinetics and metabolism because the biological matrices (proteins, nucleic, e.g.) display complex three-dimensional structures that are capable of recognizing specifically a drug molecule in only one of the many possible arrangements in the three dimensional space, thus determining the binding mode and the affinity of a drug molecule.

Asymmetric synthesis via metal catalysts and chiral ligands is one of the most elegant and effective methods for preparation of chiral compounds. Chemists have developed numerous asymmetric catalytic transformations that convert prochiral substrates into chiral products with high enantioselectivities. The 2001 Nobel Prize in Chemistry was awarded to William Knowles, Ryori Noyori and Barry Sharpless for their development in this vital and challenging area.

Despite remarkable progress in asymmetric catalysis, the design and preparation of suitable chiral ligands remain a challenging task. In this thesis, novel chiral indole-phosphine oxazoline ligands have been designed and synthesized conveniently from commercially available starting materials. These ligands demonstrated high catalytic activity in Pd-catalyzed allylic substitution reactions, and excellent yields and enantionselectivities were achieved. Moreover, the ligand was utilized to afford 2-aryl substituted chromans with sterocontrol at C-2 via asymmetric allylic etherification using a novel synthetic route.

The public defense on Friday, 01 June
 

The doctoral dissertation of MSc (Science) Yu Wang "Chiral Indole Ligands: Preparation and Application in Catalytic Asymmetric Allylic Substitutions " will be publicly examined at the Faculty of Science and Environmental Engineering of Tampere University of Technology in Sähkötalo Building, Auditorium S1 (address: Korkeakoulunkatu 8, Tampere, Finland) on Friday 1st of June 2012, at 12:00.

The opponent will be Professor Kalman J. Szabo (Department of Organic Chemistry, Stockholm University). Professor Robert Franzén of Department of Chemistry and Bioengineering (TUT) is the supervisor of this Thesis.

Yu Wang (30) is from Shenyang, China, and works as a researcher at Department of Chemistry and Bioengineering, TUT.

Further information: Yu Wang, tel. 045 355 8810; E-mail: yu.wang@tut.fi.