In Pursuit of β-Amino-α-nitro-β-(trifluoromethyl) Ketones: Nitro-Mannich versus Mannich-Type Reactions

被引：10
|
作者：
Pelagalli, Alessia [1 ]
Pellacani, Lucio [1 ]
Fioravanti, Stefania [1 ]
机构：
[1] Univ Roma La Sapienza, Dipartimento Chim, Ple Aldo Moro 5, I-00185 Rome, Italy
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 23期
关键词：
Addition; Nitro ketones; Organocatalysis; Green chemistry; Aldimines; Ketones; Stereoselctivity; AZA-HENRY REACTIONS; TRIFLUOROMETHYL ALDIMINES; STEREOSELECTIVE-SYNTHESIS; SOLVENTLESS CONDITIONS; AMINO-ACID; IMINES; DIARYLPROLINOL; DERIVATIVES; HYDRAZONES; ALDEHYDES;
D O I：
10.1002/ejoc.201700510
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactivity of -nitro ketones with trifluoromethyl aldimines has been studied for the first time. Whereas under nitro-Mannich conditions only the facial stereoselectivity can be controlled, organocatalysed Mannich-type reactions allowed complete control of the absolute and relative stereoselectivity, leading to highly functionalised -amino--nitro--(trifluoromethyl) compounds as diastereomerically pure compounds. The structures of the reactants play a key role in the geometrical and/or facial stereoselectivity.
引用
收藏
页码：3373 / 3380
页数：8
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