RECENT LABWORK

In enantioselective synthesis /stereoselective synthesis one or more new and desired element of chirality can be introduced in the organic molecule. This is important in the field of drug & natural product synthesis because the different enantiomers or diastereomers of a molecule often have different biological activity. As many others working in the field, we are also interested at TUT in industrially important reaction-types such as Michael additions and aminations. Recently, we introduced a new type of chiral ligand (based on the indole core)
with use in selected organic transformations.

Recent papers (2010 - 2012) :

"Synthesis of 2-Aryl-substituted Chromans by Intramolecular C-O
bond formation" (Y. Wang, R. Franzén)
Synlett 6: 925 - 929 (2012)

"Rh-IndOlefOx Catalyzed Conjugate addition / Heck-type Coupling of
organoboronics to a Lactam or a Lactone" (N. Kuuloja, M. Vaismaa, R. Franzén)
Tetrahedron 68 : 2313 - 2318 (2012)

"N1-Functionalized Indole-Phosphine Oxazoline (IndPHOX) ligands in Asymmetric
Allylic Substitutions" (Y. Wang, M. Vaismaa, K. Rissanen, R. Franzén)
Eur. J. Org. Chem. 1569 - 1576 (2012)

"Utilization of Indole-Phosphine Oxazoline (IndPHOX) ligands
in palladium-catalyzed allylic amination" (Y. Wang, A. Hämäläinen, M. Vaismaa, J. Tois, R. Franzén)
Tetrahedron : Asymmetry 22 : 524 - 529 (2011)

"Indole-olefin-oxazoline (IndOlefOx)-ligands: Synthesis and Utilization
in Asymmetric Rh-catalyzed Conjugate Addition" (N. Kuuloja, J. Tois and R. Franzén)
Tetrahedron : Asymmetry 22 : 468 - 475 (2011)

"Synthesis of Chiral Unsaturated Aminolactones using Pd-catalyzed Allylic Amination"
(A. Kallinen, J. Tois, R. Sjöholm and R. Franzén)
Tetrahedron : Asymmetry 21 : 2367 - 2371 (2010)

"Preparation of Indole-Phosphine Oxazoline (IndPHOX) ligands
and their application in allylic alkylation"
(Y. Wang, A. Hämäläinen, J. Tois and R. Franzén)
Tetrahedron : Asymmetry 21 : 2376 - 2384 (2010)

"Catalytic Asymmetric Total Synthesis of Tangutorine"
(T. Nemoto, E. Yamamoto, R. Franzén, T. Fukuyama, R. Wu, T. Fukamachi, H. Kobayashi and Y. Hamada)
Org. Lett. 12 : 872 - 875 (2010)

LIST OF Ph.D / Dr. Tech. Thesis

2012

"Chiral Indole ligands : Preparation and
Application in Catalytic Asymmetric Allylic Substitutions"
by Yu Wang (ISBN 978-952-15-2826-2)

"Organoboron Compounds: Substrates for Suzuki-Miyaura
Cross-Coupling and Asymmetric Conjugate Addition"
by Noora Kuuloja (ISBN 978-952-15-2775-3)

2011

"Preparation of C-C and C-N Bonds by Palladium
and Copper Catalyzed Cross-Coupling Reactions Utilizing Bidentate N,N-Ligands"
by Tuula Kylmälä (ISBN 978-952-15-2551-3)



Recently written MSc Thesis in the field of synthesis at TUT (2008 - 2012) :


" Indole-Oxazoline Ligands: Synthesis and Applications in Selected C-C Bond Formations"
written by Matti Kasurinen (2012)

" The seven-membered ring in benzodiazepines " written by Noora Katila (2011)

" Palladium-catalyzed allylic amination and Mitsunobu reaction : Two methods for synthesis of
benzyl 1,3-diphenylprop-2-enyl amines " written by Mikael Salokannas (2011)

" Asymmetric conjugate addition of diethyl malonate to nitrostyrene " written by Antti Hämäläinen (2010)

" Synthesis of La-linked BINOL and its use in the Michael addition " written by Lea Niiranen (2009)

" Michael addition catalyzed by Nickel(II)-Diamine complexes " written by Jukka Kohtamäki (2008)


updated 12/2012