Highly diastereo- and enantioselective direct Barbas-List aldol reactions promoted by novel benzamidoethyl and benzamidopropyl prolinamides in water

被引：34
|
作者：
Pedrosa, Rafael [1 ]
Andres, Jose M.
Manzano, Ruben
Roman, David
Tellez, Silvia
机构：
[1] Univ Valladolid, Fac Ciencias, Inst CINQUIMA, E-47011 Valladolid, Spain
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 03期
关键词：
SMALL ORGANIC-MOLECULES; COMPATIBLE ORGANOCATALYSTS; RECYCLABLE ORGANOCATALYST; N-PROLYLSULFONAMIDE; PROLINE DERIVATIVES; SMALL PEPTIDES; AMINO-ACIDS; EFFICIENT; ALDEHYDES; SYN;
D O I：
10.1039/c0ob00688b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Four novel benzamido-functionalized prolinamides have been prepared and tested as organocatalysts for enantioselective aldol reaction of aldehydes and cyclic ketones in water. In particular, prolinamide derived from achiral ethylene diamine was the best catalyst leading to anti aldols in excellent diastereomeric (up to 98/2) and enantiomeric (up to 99/1) ratios, thereby showing that lateral amide functionalities might be a key issue for facilitating "in water" chemistry. These catalysts are cheaper and easier to prepare than those previously described.
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收藏
页码：935 / 940
页数：6
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