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
收藏
页码：5823 / 5829
页数：7
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