Efficient asymmetric synthesis of novel gastrin receptor antagonist AG-041R via highly stereoselective alkylation of oxindole enolates

被引：89

作者：

Emura, Takashi

Esaki, Toru

Tachibana, Kazutaka

Shimizu, Makoto

机构：

[1] Chugai Pharmaceut Co Ltd, Chem Res Dept 1, Shizuoka 4128513, Japan

[2] Mie Univ, Grad Sch Engn, Dept Chem Mat, Tsu, Mie 5148507, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 22期

关键词：

D O I：

10.1021/jo061541v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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页码：8559 / 8564

页数：6

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