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Sulfoxide–Alkene Hybrids: A New Class of Chiral Ligands for the Hayashi–Miyaura Reaction

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posted on 17.06.2011, 00:00 by Tobias Thaler, Li-Na Guo, Andreas K. Steib, Mihai Raducan, Konstantin Karaghiosoff, Peter Mayer, Paul Knochel
Sulfoxide–alkene hybrids are introduced as a new class of chiral heterodentate ligands for the Hayashi–Miyaura reaction. The synthesis of these ligands was achieved without the use of protecting groups. A chiral resolution was performed via simple column-chromatographic separation of the diastereomeric ligands. Both diastereomers proved to be excellent ligands in Rh-catalyzed 1,4-addition reactions, furnishing chiral products with high enantioselectivities and, remarkably, opposite stereoconfigurations.