通过可见光光氧化还原催化合成（±）-丁苯那嗪
Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis.
作者信息
Orgren Lindsey R, Maverick Emily E, Marvin Christopher C
机构信息
Department of Chemistry, Hendrix College , 1600 Washington Avenue, Conway, Arkansas 72032, United States.
出版信息
J Org Chem. 2015 Dec 18;80(24):12635-40. doi: 10.1021/acs.joc.5b02199. Epub 2015 Nov 13.
Abstract
(±)-Tetrabenazine was synthesized in six steps from commercially available compounds. The key cyclization substrate was assembled rapidly via Baylis-Hillman and aza-Michael reactions. Annulation of the final ring was achieved through visible light photocatalysis, wherein carbon-carbon bond formation was driven by the oxidation of a tertiary amine. Solvent played a critical role in the photoredox cyclization outcome, whereas methanol led to a mixed ketal, acetonitrile/water (10:1) gave direct cyclization to (±)-tetrabenazine and occurred more rapidly.
摘要
（±）-丁苯那嗪由市售化合物经六步合成。关键的环化底物通过贝利斯-希尔曼反应和氮杂迈克尔反应快速组装而成。最后一个环的环合通过可见光光催化实现，其中碳-碳键的形成由叔胺的氧化驱动。溶剂在光氧化还原环化结果中起关键作用，甲醇导致形成混合缩酮，乙腈/水（10:1）直接环化生成（±）-丁苯那嗪且反应更快。
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