Although the indole core has been investigated for over a century, it has gained attention as a ligand only very recently. Excellent results for the utility of achiral indolylphosphine ligands in Pd-catalyzed reactions, such as Suzuki-Miyaura couplings, Hiyama cross-couplings, cross-couplings utilizing organotitanium nucleophiles, and aminations have been reported. However, only a few chiral indole ligands have been prepared until today. In comparison with other benzofused heterocycles, the selective modification methods for indole are much more diverse and thus offer more possibilities for tuning the electronic and steric properties. Also due to the accessible diversity, tunability, and potential activity in asymmetric reactions, we have recently developed many indole-phosphine oxazoline (IndPHOX) 1,2 and indole-olefin oxazoline (IndOlefOx) 3 ligands as valuable additions to oxazoline ligands. This presentation will focus on these novel ligands as alternatives in enantioselective transformations(1) Wang, Y.; H�m�l�inen, A.; Tois, J.; Franz�n, R. Tetrahedron: Asymmetry, 2010  , 21, 2376.(2) Wang, Y.; Vaismaa, M.; H�m�l�inen, A.; Tois, J.; Franz�n, R. Tetrahedron: Asymmetry, 2011  , 22, 524-529.(3) N. Kuuloja; Tois, J.; Franz�n, R. Tetrahedron: Asymmetry, 2011  , 22, 468-475.

Synthesis and applications of chiral ligands based upon an indole core

243rd National Meeting (2012)

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