Synthesis of a bulky and electron-rich derivative of SEGPhos and its application in Ru-catalyzed enantioselective hydrogenation of beta-ketoesters.

The synthesis and resolution of a bulky and electron-rich derivative of SEGPhos and its application in Ru-catalyzed asymmetric hydrogenation reaction of beta-ketoesters are reported. Up to 99.5% ee was achieved. Under solvent-free reaction conditions, acetoacetates could be reduced with good enantioselectivity and high efficiency; a TON of 20 000 was obtained within 3.5 h. The results obtained were comparable to those when SEGPhos was applied.