共 88 条
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
来源:
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.
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页码:5987 / 5995
页数:9
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