Nitrated Confined Imidodiphosphates Enable a Catalytic Asymmetric Oxa-Pictet-Spengler Reaction

被引：70

作者：

Das, Sayantani ^{[1
]}

Liu, Luping ^{[1
]}

Zheng, Yiying ^{[1
]}

Alachraf, M. Wasim ^{[1
]}

Thiel, Walter ^{[1
]}

De, Chandra Kanta ^{[1
]}

List, Benjamin ^{[1
]}

机构：

[1] Max Planck Inst Kohlenforsch, Kaiser Wilhelm Pl 1, D-45470 Mulheim, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 30期

基金：

欧洲研究理事会;

关键词：

CHIRAL BRONSTED ACIDS; FRIEDEL-CRAFTS REACTION; ENANTIOSELECTIVE SYNTHESIS; PHOSPHORIC-ACIDS; STEREOSELECTIVE-SYNTHESIS; ISOQUINOLINE ALKALOIDS; OXOCARBENIUM IONS; DISULFONIMIDE; DERIVATIVES; CYCLIZATION;

D O I：

10.1021/jacs.6b06626

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of a highly enantioselective catalytic oxa-Pictet-Spengler reaction has proven a great challenge for chemical synthesis. We now report the first example of such a process, which was realized by utilizing a nitrated confined imidodiphosphoric acid catalyst. Our approach provides substituted isochroman derivatives from both aliphatic and aromatic aldehydes with high yields and excellent enantioselectivities. DFT calculations provide insight into the reaction mechanism.

引用

页码：9429 / 9432

页数：4

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