Noscapine-derived β-amino alcohols as new organocatalysts for enantioselective addition of diethylzinc to aldehydes

被引：10

作者：

Mohebbi, Maryam ^{[1
]}

Salehi, Peyman ^{[1
]}

Bararjanian, Morteza ^{[1
]}

Ebrahimi, Samad N. ^{[1
]}

机构：

[1] Shahid Beheshti Univ, Med Plants & Drugs Res Inst, Dept Phytochem, GC, Tehran 1983963113, Iran

来源：

JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2018年 / 15卷 / 01期

基金：

美国国家科学基金会;

关键词：

Noscapine; beta-Amino alcohol; Asymmetric reaction; Diethylzinc; Macromodel; CINCHONA ALKALOIDS; ASYMMETRIC ADDITION; LIGANDS; KETONES; AMINATION;

D O I：

10.1007/s13738-017-1207-9

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this paper, synthesis of two derivatives of noscapine and their application as organocatalysts in the asymmetric addition of diethylzinc to aromatic aldehydes is reported. The first catalyst (2) was synthesized by the reduction of lactone ring of noscapine to form the corresponding diol, and the second one (3) was prepared by tert-butyl dimethyl silylation of the primary hydroxyl group of 2. Excellent yields and high ees up to 95% were obtained by using 3 as the catalyst. To the best of our knowledge, this is the first report on the application of lactone ring opened noscapinoid compounds as organocatalysts in asymmetric reactions.

引用

页码：47 / 53

页数：7

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