Asymmetric Synthesis of Vabicaserin via Oxidative Multicomponent Annulation and Asymmetric Hydrogenation of a 3,4-Substituted Quinolinium Salt

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• 作者：Vladimir Dragan ; J. Christopher McWilliams ; Ross Miller ; Karen Sutherland ; John L. Dillon ; Michael K. O鈥橞rien
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：June 21, 2013
• 年：2013
• 卷：15
• 期：12
• 页码：2942-2945
• 全文大小：227K
• 年卷期：v.15,no.12(June 21, 2013)
• ISSN：1523-7052

文摘

An efficient, asymmetric synthesis of the 5-HT_2C agonist vabicaserin in four chemical steps and 54% overall yield from commercially available benzodiazepine was achieved. The synthesis was highlighted by a novel oxidative, multicomponent reaction to affect the quinolinium ring assembly in one step followed by an unprecedented asymmetric hydrogenation of a 3,4-substituted quinolinium salt.