An Enantioselective Recyclable Polystyrene-Supported Threonine-Derived Organocatalyst for Aldol Reactions

被引：29
|
作者：
Henseler, Andrea H. [1 ]
Ayats, Carles [1 ]
Pericas, Miquel A. [1 ,2 ]
机构：
[1] Inst Chem Res Catalonia ICIQ, E-43007 Tarragona, Spain
[2] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 08期
关键词：
aldol reaction; amino acids; organocatalysis; polymers; supported catalysts; SILOXY SERINE ORGANOCATALYST; HIGHLY EFFICIENT ORGANOCATALYSTS; ASYMMETRIC MICHAEL ADDITION; SELECTIVE MANNICH REACTIONS; CONTINUOUS-FLOW PRODUCTION; ACYCLIC AMINO-ACIDS; SYN-ALDOL; ALPHA-AMINOXYLATION; L-PROLINE; ENOLIZABLE ALDEHYDES;
D O I：
10.1002/adsc.201400033
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A series of primary amino acids covalently supported onto polystyrene through alkyne-azide cycloaddition reactions has been synthesized and evaluated as catalysts in asymmetric aldol reactions. A polymer-supported threonine behaves as an easily recyclable, highly reactive and stereoselective (up to 99% ee) catalyst in the aldol reaction of both cyclic and acyclic ketone donors with aromatic aldehydes in aqueous environments. While cyclic ketones react with anti diastereoselectivity, syn adducts are predominantly obtained with acyclic substrates. The heterogenized threonine catalyst has been used for the sequential synthesis of a small library of enantiopure aldol products.
引用
收藏
页码：1795 / 1802
页数：8
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