Synthesis of Tetrahydroisoquinolines Through an Iron-Catalyzed Cascade: Tandem Alcohol Substitution and Hydroamination
Synthesis of Tetrahydroisoquinolines Through an Iron-Catalyzed Cascade: Tandem Alcohol Substitution and Hydroamination
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DOI：
10.1021/acs.orglett.9b02353
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发表时间：
2019-09-06
期刊：
影响因子：
5.2
通讯作者：
Cook, Silas P.
中科院分区：
文献类型：
--
作者：
Marcyk, Paul T.;Cook, Silas P.
饱和氮杂环化合物的快速组装--合成上更具挑战性的芳香族化合物变体--可以加速生物相关分子的合成。从与未活化的烯烃连接的苄醇开始，铁催化的串联醇取代和加氢胺化在单个合成步骤中提供了获得四氢异喹啉的途径。使用温和的铁基催化剂，这些操作的组合形成了两个碳-氮键，并提供了一种独特的成环策略来获得这种有价值的核心。
Rapid assembly of saturated nitrogen heterocycles-the synthetically more challenging variants of their aromatic relatives-can expedite the synthesis of biologically relevant molecules. Starting from a benzylic alcohol tethered to an unactivated alkene, an iron-catalyzed tandem alcohol substitution and hydroamination provides access to tetrahydroisoquinolines in a single synthetic step. Using a mild iron-based catalyst, the combination of these operations forms two carbon-nitrogen bonds and provides a unique annulation strategy to access this valuable core.