Diastereoselective synthesis of trans-2-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropanecarboxylic acids: key intermediates for the preparation of potent and chiral histamine H3 receptor agents
Diastereoselective synthesis of trans-2-(1-triphenylmethyl-1H-imidazol-4-yl)cyclopropanecarboxylic acids: key intermediates for the preparation of potent and chiral histamine H3 receptor agents
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反式2-(1-三苯甲基-1H-咪唑-4-基)环丙烷甲酸的非对映选择性合成：制备强效手性组胺H3受体药物的关键中间体
DOI：
10.1016/s0960-894x(97)10137-8
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发表时间：
1997
影响因子：
2.7
通讯作者：
J. Phillips
中科院分区：
文献类型：
--
作者：
M. A. Khan;S. L. Yates;C. Tedford;K. Kirschbaum;J. Phillips
介绍了trans-2-(1-triphenylmethyl-1H-imidazol-4-yl)-cyclopropanecarboxylic酸的两种对映体的制备方法。合成的关键步骤是用三甲基亚砜叶立德对(5R)-trans-4-aza-10，10-dimethyl-3-thia-4-(3-(1-triphenylmethyl-1H-imidazol-4-yl)prop-2-enoyl)tricyclo[5.2.1.0<；1，5>；]decane-3，3-dione进行3：1的非对映选择性环丙烷化反应。这些环丙烷可用于H3受体试剂的制备。
Procedures for the preparation of both enantiomers of trans-2-(1-triphenylmethyl-1H-imidazol-4-yl)-cyclopropanecarboxylic acid are described. The key step in the synthesis is a 3:1 diastereoselective cyclopropanation of (5R)-trans-4-aza-10,10-dimethyl-3-thia-4-(3-(1-triphenylmethyl-1H-imidazol-4-yl)prop-2-enoyl)tricyclo[5.2.1.0<1,5>]decane-3,3-dione using trimethylsulfoxonium ylide. These cyclopropanes are useful for the preparation of H3receptor agents.