Efficient asymmetric synthesis of novel gastrin receptor antagonist AG-041R via highly stereoselective alkylation of oxindole enolates
Efficient asymmetric synthesis of novel gastrin receptor antagonist AG-041R via highly stereoselective alkylation of oxindole enolates
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DOI：
10.1021/jo061541v
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发表时间：
2006-10-27
影响因子：
3.6
通讯作者：
Shimizu, Makoto
中科院分区：
文献类型：
--
作者：
Emura, Takashi;Esaki, Toru;Shimizu, Makoto
建立了一种高效的胃泌素/CCK-B受体拮抗剂AG-041R的不对称合成方法。以L薄荷醇为手性助剂，通过氧吲哚烯醇酸酯与溴乙酸酯的不对称烷基化反应，建立了核心氧吲哚立体化学。氧化吲哚烯醇酸酯的关键烷基化反应生成了具有高非对映选择性的四取代手性中间体。详细描述了立体选择性烷基化反应。
An efficient method for asymmetric synthesis of the potent Gastrin/CCK-B receptor antagonist AG-041R was developed. Core oxindole stereochemistry was established by asymmetric alkylation of oxindole enolates with bromoacetic acid esters, using l-menthol as a chiral auxiliary. The key alkylation reaction of the oxindole enolates generated tetrasubstituted chiral intermediates with high diastereoselectivity. The stereoselective alkylation reactions are described in detail.