Cyanomethylation of b-Alkoxyaldehydes: Toward a Short Synthesis of Atorvastatin
Cyanomethylation of b-Alkoxyaldehydes: Toward a Short Synthesis of Atorvastatin
复制标题
b-烷氧基醛的氰甲基化：阿托伐他汀的简短合成
DOI：
10.1002/ajoc.201900595
复制
发表时间：
2020
期刊：
影响因子：
--
通讯作者：
M.
中科院分区：
文献类型：
--
作者：
Kumar;R. T.; Noda;H.; Shibasaki;M.
描述了β‐烷氧醛的氰甲基化反应。由于竞争的消除和添加途径，这些易于消除的底物构成了化学选择性问题。虽然许多常用的强Brønsted碱有利于消除，但nBuLi有效地促进了α‐氰化碳离子的加入并抑制了不希望的消除。氰甲基化产物可转化为合成立普妥活性药物成分阿托伐他汀的已知中间体，显示了当前转化的合成潜力。
The cyanomethylation of β‐alkoxyaldehydes is described. These elimination‐prone substrates pose a chemoselectivity issue due to the competing elimination and addition pathways. While many commonly used strong Brønsted bases favor elimination,nBuLi effectively promotes the addition of an α‐cyanocarbanion and suppresses the undesired elimination. The cyanomethylated product can be converted to a known intermediate for the synthesis of atorvastatin, an active pharmaceutical ingredient of Lipitor, showcasing the synthetic potential of the current transformation.