Enantioselective Synthesis of 4-Isoxazolines by 1,3-Dipolar Cycloadditions of Nitrones to Alkynals Catalyzed by Fluorodiphenylmethylpyrrolidines

被引：43

作者：

Aleman, Jose ^{[1
]}

Fraile, Alberto ^{[1
]}

Marzo, Leyre ^{[1
]}

Ruano, Jose Luis Garcia ^{[1
]}

Izquierdo, Cristina ^{[1
]}

Diaz-Tendero, Sergio ^{[2
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ Modulo 1, E-28049 Madrid, Spain

[2] Univ Autonoma Madrid, Dept Quim Modulo 13, E-28049 Madrid, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 09期

关键词：

3+2]?cycloaddition reactions; 2; 3-dihydroisoxazoles; iminium ions; 4-isoxazolines; organocatalysis; ONE-POT; ALKYNYLZINC REAGENTS; EFFICIENT SYNTHESIS; ALLENES; 2,3-DIHYDROISOXAZOLES; DELTA-4-ISOXAZOLINES; ACYLAZIRIDINES; TRANSFORMATION; PRECURSORS; INHIBITORS;

D O I：

10.1002/adsc.201200033

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The first organocatalytic enantioselective 1,3-dipolar reaction between nitrones and alkynals catalyzed by (S)-2-(fluorodiphenylmethyl)pyrrolidine to give 4-isoxazolines (2,3-dihydroisoxazoles) with high enantiomeric excess, excellent yields and low catalyst loading (15 mol%) is presented. The catalytic loading could be reduced to 1 mol% with only slight increases in reaction times.

引用

页码：1665 / 1671

页数：7

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