Proline dipeptides containing fluorine moieties as oganocatalysts for the asymmetric aldol reaction

被引:14
作者
Ahmetlli, Ardiol [1 ]
Spiliopoulou, Nikoleta [1 ]
Magi-Oikonomopoulou, Angeliki [1 ]
Gerokonstantis, Dimitrios-Triantaffylos [1 ]
Moutevelis-Minakakis, Panagiota [1 ]
Kokotos, Christoforos G. [1 ]
机构
[1] Univ Athens, Dept Chem, Lab Organ Chem, Athens 15771, Greece
关键词
Aldol reaction; Organocatalysis; Prolinamides; Dipeptides; Fluorine; PEPTIDE-BASED CATALYSTS; TERT-BUTYL ESTERS; AMINO-ACIDS; ORGANIC CATALYSTS; AQUEOUS-MEDIA; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; ENANTIOSELECTIVE ALDOL; VERSATILE CATALYSTS; BINAM-PROLINAMIDES; HIGHLY EFFICIENT;
D O I
10.1016/j.tet.2018.08.038
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of dipeptide analogues consisting of proline, phenylalanine and aniline- or phenol-fluorine derivatives were synthesized. Their catalytic ability was evaluated in the intermolecular asymmetric aldol reaction, both in organic and aqueous media. Aniline-fluorine derivatives proved to be superior and the best results were obtained, when 2-CF3 aniline was employed. A diverse substrate scope consisting of both aromatic and aliphatic aldehydes, as well as different ketones was demonstrated, where aromatic aldehydes afforded products in high yields (up to 100%) with excellent diastereo- (up to 95:5) and enantioselectivities (up to 97%), whereas the aliphatic aldehydes afforded also excellent selectivities, but relatively low yield. A simple addition of fluorine to a dipeptide analogue affords organocatalysts with new interesting properties that can catalyze the aldol reaction more efficiently. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5987 / 5995
页数:9
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