Gold-Catalyzed Synthesis of Spirofused Indoloquinuclidines

被引：19

作者：

Glinsky-Olivier, Nicolas ^{[1
]}

Retailleau, Pascal ^{[1
]}

Guinchard, Xavier ^{[1
]}

机构：

[1] Univ Paris Saclay, Univ Paris Sud, CNRS UPR 2301, Inst Chim Subst Nat, 1 Av Terrasse, F-91198 Gif Sur Yvette, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 42期

关键词：

Homogenous catalysis; Organocatalysis; Asymmetric catalysis; Alkaloids; Spiro compounds; PICTET-SPENGLER REACTION; TETRAHYDRO-BETA-CARBOLINES; BRONSTED ACID CATALYSTS; GOLD(I)-CATALYZED CARBOAMINATIONS; TANDEM DEPROTECTION/CYCLIZATION; REACTIVITY; COMPLEX; DEAROMATIZATION; HYDROAMINATION; HYDROGENATION;

D O I：

10.1002/ejoc.201800357

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel series of spirofused indoloquinuclidines was obtained by a tandem Pictet-Spengler/Au-I-catalyzed cyclization sequence. By combining N-propargyl tryptamine with aldehydes in the presence of acetic acid and a gold complex, the target indoloquinuclidines were obtained. The combination of a chiral phosphoric acid catalyst for the asymmetric Pictet-Spengler reaction with a gold complex furnished the target compounds with ee values up to 90 % in high diastereoselectivity.

引用

页码：5823 / 5829

页数：7

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