Regio-, Diastereo-, and Enantioselective Organocatalytic Addition of 4-Substituted Pyrazolones to Isatin-Derived Nitroalkenes

被引：15

作者：

Vila, Carlos ^{[1
]}

Raj Dharmaraj, Nisshanth ^{[1
]}

Faubel, Antonio ^{[1
]}

Blay, Gonzalo ^{[1
]}

Luz Cardona, M. ^{[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：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 19期

关键词：

Asymmetric catalysis; Nitroalkenes; Pyrazolones; Organocatalysis; Nucleophilic substitution; GROWTH-FACTOR RECEPTOR; STEREOCONTROLLED CONSTRUCTION; OXINDOLE ALKALOIDS; MICHAEL ADDITION; PYRAZOL-5-ONES; PYRAZOLIN-5-ONES; ALKYLATION; QUATERNARY; REACTIVITY; INHIBITORS;

D O I：

10.1002/ejoc.201900328

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether [(DHQ)(2)Pyr] catalyzed the regio-, diastereo-, and enantioselective addition of 4-substituted pyrazolones to isatin-derived nitroalkenes, providing a variety of chiral alkenylpyrazolone adducts containing a tetrasubstituted stereocenter bearing an oxindole moiety with excellent yields, regioselectivity, and diastereoselectivity, as well as a moderate enantioselectivity (up to 98 % yield, > 20:1 E/Z ratio dr and 78 % ee). The reaction harnesses a nitroalkene as an alkenylating agent through a Nucleophilic Vinylic Substitution (SNV) reaction.

引用

页码：3040 / 3044

页数：5

共 46 条

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