Catalytic Asymmetric Hydrogenation of α‐Arylcyclohexanones and Total Synthesis of (−)‐α‐Lycorane. Issue 8 (15th May 2013)

• Record Type: Journal Article
• Authors: Li, Gang; Xie, Jian‐Hua; Hou, Jing; Zhu, Shou‐Fei; Zhou, Qi‐Lin
• Is Part Of: Advanced synthesis & catalysis. Volume 355:Issue 8(2013)
• Page Start: 1597
• Page End: 1604
• Publication Date: 2013-05-15
• Subjects: Amarylliaceae alkaloids -- asymmetric catalysis -- chiral spiro catalyst -- dynamic kinetic resolution -- hydrogenation -- lycorane; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201300165
• Languages: English
• ISSNs: 1615-4150

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% overall yield over 13 steps from commercially available starting material. Abstract :