Catalytic Asymmetric Hydrogenation of α??Arylcyclohexanones and Total Synthesis of (−)?螃窿?Lycorane

…, JH Xie, J Hou, SF Zhu, QL Zhou

Index: Li, Gang; Xie, Jian-Hua; Hou, Jing; Zhu, Shou-Fei; Zhou, Qi-Lin Advanced Synthesis and Catalysis, 2013 , vol. 355, # 8 p. 1597 - 1604

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Citation Number: 12

Abstract

Abstract An efficient catalytic asymmetric hydrogenation of racemic α-arylcyclohexanones with an ethylene ketal group at the 5-position of the cyclohexane ring via dynamic kinetic resolution has been developed, giving chiral α-arylcyclohexanols with two contiguous stereocenters with up to 99% ee and> 99: 1 cis/trans-selectivity. Using this highly efficient asymmetric hydrogenation reaction as a key step,(−)-α-lycorane was synthesized in 19.6 ...