Organocatalytic asymmetric synthesis of highly functionalized pyrrolizidines via cascade Michael/hemi-aminalization reactions of isoindolinones

被引：16

作者：

Scorzelli, Francesco ^{[1
]}

Di Mola, Antonia ^{[1
]}

Croce, Gianluca ^{[2
]}

Palombi, Laura ^{[1
]}

Massa, Antonio ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim & Biol, I-84084 Fisciano, SA, Italy

[2] Univ Piemonte Orientate Viale T Michel, DISIT, I-15121 Alessandria, Italy

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 21期

关键词：

Nitrogen heterocycles; Isoindolinones; Pyrrolizidines; Organocatalysis; ALKALOIDS; NITROALKENES;

D O I：

10.1016/j.tetlet.2015.04.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This Letter describes the first application of activated 3-substituted isoindolinones in asymmetric synthesis of aza-tricyclic heterocycles, belonging to the class of pyrrolizidines. It was found that diphenylprolinol trimethylsilyl (TMS) ether was particularly effective, allowing the obtaining of adducts in good yields and up to 96% ee via iminium ion catalysis in the reaction of unsaturated aldehydes. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：2787 / 2790

页数：4

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