Water-compatible one-pot organocatalytic asymmetric synthesis of cyclic nitrones. Application in intramolecular 1,3-dipolar cycloadditions

被引：15

作者：

Sadaba, David ^{[1
]}

Delso, Ignacio ^{[1
,2
]}

Tejero, Tomas ^{[1
]}

Merino, Pedro ^{[1
]}

机构：

[1] Univ Zaragoza, Dept Quim Organ, CSIC, ISQCH,Lab Sintesis Asimetr, E-50009 Zaragoza, Aragon, Spain

[2] Univ Zaragoza, Ctr Quim & Mat Aragon CEQMA, NMR Serv, CSIC, E-50009 Zaragoza, Aragon, Spain

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 45期

关键词：

Nitrones; Intramolecular dipolar cycloaddition; Pyrrolidines; Michael addition; Organocatalysis; STEREOSELECTIVE-SYNTHESIS; EN-ROUTE; MICHAEL REACTION; FORMAL SYNTHESIS; PYRROLIDINE; NITROALKENES; ALDEHYDES; PYRROLIZIDINE; INDOLIZIDINE; ADDITIONS;

D O I：

10.1016/j.tetlet.2011.08.138

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active five-membered cyclic nitrones are readily obtained in a one-pot procedure via the organocatalytic Michael addition of aldehydes to nitroolefins and in situ reductive cyclization. Application of the methodology to the synthesis of tricyclic compounds through intramolecular 1,3-dipolar cycloaddition reactions (DFT calculations have also been performed) is also demonstrated. All the reactions were carried out in water as a solvent and excellent ee values (ee >99%) were obtained. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：5976 / 5979

页数：4

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