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

被引：17

作者：

Dragan, Vladimir ^{[1
]}

McWilliams, J. Christopher ^{[1
]}

Miller, Ross ^{[1
]}

Sutherland, Karen ^{[1
]}

Dillon, John L. ^{[2
]}

O'Brien, Michael K. ^{[1
]}

机构：

[1] Pfizer Inc, Pharmaceut Sci, Groton, CT 06340 USA

[2] Pfizer Inc, Global Supply, Peapack, NJ 07970 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 12期

关键词：

HIGHLY ENANTIOSELECTIVE HYDROGENATION; IRIDIUM-CATALYZED HYDROGENATION; ACCESS; DERIVATIVES;

D O I：

10.1021/ol401029k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, asymmetric synthesis of the 5-HT2C 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.

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收藏

页码：2942 / 2945

页数：4

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