Domino-Sonogashira/Carbopalladation/CH-activation reaction for the synthesis of molecular switches.
|
The development of efficient and selective as well as ecologically and economically benifical synthetic procedures is
a major goal in modern organic synthesis. We have introduced the concept of domino reactions into science which
has shown its high potential in recent years. Thus, it allows the preparation of complex molecules starting from
simple substrates under identical conditions with excellent atom and step economy. Moreover, for the synthesis of
substance libraries the use of multicomponent domino reactions is highly advantageous. The procedure is employed by us
in the synthesis of natural products and materials as electronic switches and motors.
Typical domino reactions developed by us are the domino-Knoevenagel/hetero-Diels-Alder, the domino-Knoevenagel/ene,
the domino-amidation/imine formation/electrophilic substitution, the domino-oxiran ring opening/Brook rearrangement,
the enantioselective domino-Wacker/Heck, the enantioselective domino-Wacker/carbonylation/methylation, the domino-carbopalladation/Stille
and the domino-carbopalladation/CH-activation reaction. Moreover, we have developed a highly selective domino-allylation of aldehydes and ketones to give enantiopure homoallylic ethers. Domino-Sonogashira/Carbopalladation/CH-activation reaction for the synthesis of molecular switches. |
| Overview: L.F. Tietze (Ed.) | Domino Reactions: Concepts for Efficient Organic Synthesis, Wiley-VCH, Weinheim, 2014, (ISBN: 3-527-33432-7, ISBN-13: 978-3527334322). | |
| L.F. Tietze, J. Clerc, S. Biller, S.-C. Duefert, M. Bischoff | Enantioselective Total Synthesis of the Lignan (+)-Linoxepin.
Chem. Eur. J. 2014, 20, 17119–17124. |
|
| L.F. Tietze, C. Eichhorst, T. Hungerland, M. Steinert | A Fast Way to Fluorescence: A Fourfold Domino Reaction to Condensed Polycyclic Compounds.
Chem. Eur. J. 2014, 20, 12553-12558. |
|
| L.F. Tietze, S. Jackenkroll, J. Hierold, L. Ma, B. Waldecker | A Domino Approach to the Enantioselective Total Syntheses of Blennolide C and Gonytolide C. Chem. Eur. J.
2014, 20, 8628-8635. |
|
| L.F. Tietze, S. Jackenkroll, C. Raith, D.A. Spiegl, J.R. Reiner, M.C. Ochoa Campos | Enantioselective Total Synthesis of (-)-Diversonol.
Chem. Eur. J. 2013, 19, 4876-4882. |
|
| L.F. Tietze, T. Hungerland, C. Eichhorst, A. Düfert, C. Maaß, D. Stalke | Efficient Synthesis of Helical Tetrasubstituted Alkenes as Potential Molecular Switches: A Two-Component Palladium-Catalyzed Triple Domino Process.
Angew. Chem. 2013, 125, 3756-3759;
Angew. Chem., Int. Ed. 2013, 52, 3668-3671. |
|
| L.F. Tietze, S.-C. Duefert, J. Clerc, M. Bischoff, C. Maaß, D. Stalke | Total Synthesis of Linoxepin through a Palladium-Catalyzed Domino Reaction.
Angew. Chem. 2013, 125, 3273-3276;
Angew. Chem., Int. Ed. 2013, 52, 3191-3194. |
|
| L.F. Tietze, A. Düfert, F. Lotz, L. Sölter, K. Oum, T. Lenzer, T. Beck, R. Herbst-Irmer | Synthesis of Chiroptical Molecular Switches by Pd-Catalyzed Domino Reactions.
J. Am. Chem. Soc. 2009, 131, 17879–17884. |
|
| L.F. Tietze, T. Kinzel, C. Brazel | The Domino Multicomponent Allylation Reaction for the Stereoselective Synthesis of Homoallylic Alcohols.
Acc. Chem. Res. 2009, 42, 367–378. |
|
| L.F. Tietze, T. Kinzel, S. Schmatz | Determination of the Origin of Stereoselectivity in Multiple-Transition-State Reactions Using DFT Calculations:
Enantioselective Synthesis of Homoallylic Alcohols from Aliphatic Methyl Ketones via an Auxiliary-Mediated Allylation.
J. Am. Chem. Soc. 2008, 130, 4386-4395. |
|