An atom efficient synthesis of tamoxifen

被引：7

作者：

Heijnen, Dorus ^{[1
]}

van Zuijlen, Milan ^{[1
]}

Tosi, Filippo ^{[1
]}

Feringa, Ben L. ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst Chem, Nijenborgh 4, NL-9747 AG Groningen, Netherlands

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 09期

基金：

欧洲研究理事会;

关键词：

3-COMPONENT COUPLING REACTION; STEREOSELECTIVE-SYNTHESIS; GRIGNARD-REAGENTS; INTRAMOLECULAR CARBOLITHIATION; ORGANOLITHIUM COMPOUNDS; ARYL HALIDES; PALLADIUM; ALKYNES; (Z)-TAMOXIFEN; DERIVATIVES;

D O I：

10.1039/c8ob02977f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct carbolithiation of diphenylacetylenes and their cross-coupling procedure taking advantage of the intermediate alkenyllithium reagents are presented. By employing our recently discovered highly active palladium nanoparticle based catalyst, we were able to couple an alkenyllithium reagent with a high (Z/E) selectivity (10 : 1) and good yield to give the breast cancer drug tamoxifen in just 2 steps from commercially available starting materials and with excellent atom economy and reaction mass efficiency.

引用

页码：2315 / 2320

页数：6

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