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手性铜配合物的不对称硝基醇醛缩合反应。

Heterogeneous chiral copper complexes of amino alcohol for asymmetric nitroaldol reaction.

机构信息

Discipline of Inorganic Materials & Catalysis, Central Salt and Marine Chemicals Research Institute, Council of Scientific & Industrial Research, Bhavnagar-364 002, Gujarat, India.

出版信息

J Org Chem. 2010 Sep 17;75(18):6191-5. doi: 10.1021/jo1010679.

DOI:10.1021/jo1010679
PMID:20722371
Abstract

Chiral amino alcohols supported on mesoporous silicas were synthesized and evaluated as a new class of chiral ligands in copper-catalyzed nitroaldol reaction under heterogeneous and mild reaction conditions. The activity and enantioselectivity of the present catalytic system is immensely influenced by the presence of achiral and chiral bases as an additive. The heterogenized chiral copper(II) complex of amino alcohol was found to be an effective recyclable catalyst for the nitroaldol reaction of different aldehydes such as aromatic, aliphatic, alicyclic, and α-β unsaturated aldehydes to produce nitroaldol products with remarkably high enantioselectivity (≥99%) and yields.

摘要

手性氨基醇负载在介孔硅上作为一种新型手性配体,在铜催化的硝酮醇缩合反应中,在非均相和温和的反应条件下进行了研究。在作为添加剂的存在下,本催化体系的活性和对映选择性受到非手性和手性碱的极大影响。手性铜(II)配合物的氨基醇被发现是一种有效的可回收催化剂,用于不同醛(如芳香族、脂肪族、脂环族和α-β 不饱和醛)的硝酮醇缩合反应,以高对映选择性(≥99%)和产率生成硝酮醇缩合产物。

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