Enantioselective Syntheses of Corynanthe Alkaloids by Chiral Bronsted Acid and Palladium Catalysis

被引：29
|
作者：
Wanner, Martin J. [1 ]
Claveau, Elise [1 ]
van Maarseveen, Jan H. [1 ]
Hiemstra, Henk [1 ]
机构：
[1] Univ Amsterdam, Vant Hoff Inst Mol Sci, NL-1098 XH Amsterdam, Netherlands
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2011年 / 17卷 / 49期
关键词：
alkaloids; allylation; Bronsted acids; enantioselectivity; palladium; PICTET-SPENGLER REACTIONS; SECONDARY-AMINES; INDOLE ALKALOIDS;
D O I：
10.1002/chem.201103150
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Synergistic catalysis: Three indole alkaloids (-)-corynantheidine, (+)-corynantheine and (+)-dihydro-corynantheine were prepared following a short and common strategy based on the binol phosphoric acid catalyzed enantioselective Pictet-Spengler reaction, followed by closure of the final ring by an intramolecular Tsuji-Trost-type Pd-catalyzed allylic alkylation by using an α-ketoester-derived enolate as the nucleophile (see scheme). © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：13680 / 13683
页数：4
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