Catalysis

Overview of catalysis topics covered by the Laschat Research Group

The asymmetric rhodium catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds also known as Hayashi Miyaura reaction is an important reaction for the asymmetric carbon-carbon bond formation. The reaction was first mentioned in 1997 and 1998 by Hayashi and Miyaura.[1,2]Through the preliminary studies of Hayashi, Carreira[3] and Grützmacher[4], chiral diene ligands came forward as a new class of ligands in Rh- and Ir-catalysed reactions. 
We were able to synthesize different tropane-derived phosphorus–olefin hybrid ligands 1 and disubstituted chiral diene ligands with pentalene as backbone 2 and could show successfully their application in the 1,4-addition of arylbronic acids to enones.[5,6] Therefore we are currently interested in the development of new chiral diene and phosphorous/olefin ligands and their area of applications.

[1] M. Sakai, H. Hayashi, N. Miyaura, Organometallics 199716, 4229–4231.
[2] Y. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura, J. Am. Chem. Soc. 1998120, 5579–5580.
[3] J.-F. Paquin, C. R. J. Stephenson, C. Defieber, E. M. Carreira, Org. Lett. 20057, 3821–3824.
[4] F. Läng, F. Breher, D. Stein, H.Grützmacher, Organometallics 200524, 2997–3007.
[5] S. Vlahovic, N. Schädel, S. Tussetschläger, and S. Laschat, Eur. J. Org. Chem. 2013, 1580–1590.
[6] S. Helbig, S. Sauer, N. Cramer, S. Laschat, A. Baro, W. Frey, Adv. Synth. Catal. 2007349, 2331 – 2337.

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