Catalytic Asymmetric Allylation of 3,4-Dihydroisoquinolines and Its Application to the Synthesis of Isoquinoline Alkaloids
Catalytic Asymmetric Allylation of 3,4-Dihydroisoquinolines and Its Application to the Synthesis of Isoquinoline Alkaloids
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DOI：
10.1021/jo101956m
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发表时间：
2011-01-21
影响因子：
3.6
通讯作者：
Itoh, Takashi
中科院分区：
文献类型：
--
作者：
Miyazaki, Michiko;Ando, Nami;Itoh, Takashi
以烯丙基三甲氧基硅烷-Cu为亲核试剂，在DTBM-SEGPHOS作为手性配体存在下，对3,4-二氢异喹啉进行催化不对称烯丙基化，以良好的产率和立体选择性得到相应的手性1-烯丙基四氢异喹啉衍生物。由此获得的烯丙基加合物应用于多种异喹啉生物碱的合成，例如crispine A和高洛丹诺辛。该反应进一步用于合成 schulzeine A 的异喹啉部分。
A catalytic asymmetric allylation of 3,4-dihydroisoquinoline was carried out with allyltrimethoxylsilane-Cu as the nucleophile in the presence of DTBM-SEGPHOS as the chiral ligand to afford corresponding chiral 1-allyltetrahydroisoquinoline derivatives in good yield and stereoselectivity. The allyl adduct thus obtained was applied to the synthesis of several isoquinoline alkaloids such as crispine A and homolaudanosine. The reaction was further used for the synthesis of the isoquinoline moiety of schulzeine A.