Synthesis and application of new iminopyridine ligands to enantioselective copper(II)-catalyzed Henry reaction

被引:14
作者
Solinas, Maurizio [1 ]
Sechi, Barbara [1 ]
Baldino, Salvatore [2 ]
Chelucci, Giorgio [2 ]
机构
[1] UOS Sassari, Ist Chim Biomol, CNR, I-07100 Sassari, Italy
[2] Univ Sassari, Dipartimento Agr, I-07100 Sassari, Italy
关键词
Chiral iminopyridines; Enantioselective Henry reaction; Asymmetric catalysis; beta-Nitroalcohols; Copper(II)-catalysts; Cu(OAc)(2)center dot H2O; ASYMMETRIC NITROALDOL REACTIONS; SALEN-CHROMIUM COMPLEXES; FACILE SYNTHESIS; CATALYSTS; ALDEHYDES; AMINO; BIS(THIAZOLINE); BIS(OXAZOLINE); BENZALDEHYDE; DIETHYLZINC;
D O I
10.1016/j.molcata.2013.06.008
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Chiral iminopyridines obtained by reaction between a variety of chiral amines and pyridyl aldehydes or ketones were assessed as catalysts in the enantioselective Henry reaction between nitromethane and 2-methoxybenzaldehyde in the presence of copper(II) acetate. 1-(2-Methoxyphenyl)-2-nitroethanol was obtained in moderate yields and good enantioselectivities (up to 82% ee) under straightforward experimental conditions without the need for air or moisture exclusion. The best enantioselectivity (82% ee) was obtained by an iminopyridine based on a camphane skeleton. (c) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:206 / 212
页数:7
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