Organocatalytic enantioselective aminoalkylation of pyrazol-3-ones with aldimines generated in situ from α-amido sulfones

被引：10

作者：

Carceller-Ferrer, Laura ^{[1
]}

Vila, Carlos ^{[1
]}

Blay, Gonzalo ^{[1
]}

Fernandez, Isabel ^{[1
]}

Carmen Munoz, M. ^{[2
]}

Pedro, Jose R. ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, Dr Moliner 50, E-46100 Valencia, Spain

[2] Univ Politecn Valencia, Dept Fis Aplicada, Camino Vera S-N, E-46022 Valencia, Spain

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 46期

关键词：

ASYMMETRIC MANNICH REACTIONS; N-BOC; PRECURSORS; IMINES; CONSTRUCTION; INHIBITORS; PYRAZOLES; BEARING; CBZ;

D O I：

10.1039/c9ob02252j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, an efficient asymmetric aminoalkylation of pyrazolones with alpha-amido sulfones catalyzed by a quinine-derived squaramide in dichloromethane/aqueous media has been established. A variety of chiral amines were obtained with high yields (up to 98%) and excellent enantioselectivities (up to 99% ee). The corresponding products are transformed into optically active acetylated pyrazoles after treatment with Ac2O/Et3N, because of the instability of some adducts. The reaction tolerates a wide range of alpha-amido sulfones and different pyrazolones.

引用

页码：9859 / 9863

页数：5

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