Diastereoselective hydrogenation of substituted quinolines to enantiomerically pure decahydroquinolines

M Heitbaum, R Froehlich…

Index: Heitbaum, Maja; Froehlich, Roland; Glorius, Frank Advanced Synthesis and Catalysis, 2010 , vol. 352, # 2-3 p. 357 - 362

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Citation Number: 29

Abstract

Abstract The stereoselective hydrogenation of auxiliary-substituted quinolines was used to build up saturated and partially saturated heterocycles. In a first step, the formation and diastereoselective hydrogenation of 2-oxazolidinone-substituted quinolines to 5, 6, 7, 8- tetrahydroquinolines is reported. In this unprecedented process, stereocenters on the carbocyclic quinoline ring were formed with a dr of up to 89: 11. Platinum oxide as a ...