Regioselectivity Change in the Organocatalytic Enantioselective (3+2) Cycloaddition with Nitrones through Cooperative Hydrogen-Bonding Catalysis/Iminium Activation

被引：16

作者：

Prieto, Liher ^{[1
]}

Juste-Navarro, Veronica ^{[2
]}

Uria, Uxue ^{[1
]}

Delso, Ignacio ^{[2
]}

Reyes, Efraim ^{[1
]}

Tejero, Tomas ^{[2
]}

Carrillo, Luisa ^{[1
]}

Merino, Pedro ^{[2
]}

Vicario, Jose L. ^{[1
]}

机构：

[1] Univ Basque Country UPV EHU, Dept Organ Chem 2, POB 644, Bilbao 48080, Spain

[2] Univ Zaragoza, CSIC, ISQCH, Lab Sintesis Asimetr, Campus San Francisco, Zaragoza 5009, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 12期

关键词：

asymmetric catalysis; cycloaddition; nitrones; organocatalysis; pyrrolidines; 1,3-DIPOLAR CYCLOADDITIONS; AZOMETHINE YLIDES; ASYMMETRIC-SYNTHESIS; ORGANIC CATALYSIS; ALDEHYDES; STRATEGIES; REACTIVITY; PYRROLIDINES; ETHERS;

D O I：

10.1002/chem.201605350

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of nitrones with enals through iminium activation can be modulated by using cooperative hydrogen-bonding catalysis to induce the participation of a nitrone ylide (C-N-C) instead of the classical C-N-O dipole. As a consequence, N-hydroxypyrrolidines are obtained, rather than the expected isoxazolidines. The reaction proceeds smoothly and high enantioselectivities are observed in all cases. By using the appropriate substrate, polysubstituted pyrrolidines incorporating quaternary stereocenters can be efficiently prepared.

引用

页码：2764 / 2768

页数：5

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