Synthesis of novel thiophene-based chiral ligands and their application in asymmetric Henry reaction

被引：15
作者：
Aydin, A. Ebru [1 ]
机构：
[1] Mustafa Kemal Univ, Dept Chem, TR-31040 Antakya, Turkey
来源：
APPLIED ORGANOMETALLIC CHEMISTRY | 2013年 / 27卷 / 05期
关键词：
enantioselective synthesis; Henry reaction; chiral amino alcohols; thiolated amino alcohols; copper complex; NITROALDOL REACTION; AMINO-ALCOHOLS; BIS(OXAZOLINE) LIGANDS; CATALYSIS; EFFICIENT; BIS(THIAZOLINE); DIETHYLZINC; COMPLEXES; SILICA; INDOLE;
D O I：
10.1002/aoc.2969
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Novel chiral thiolated amino alcohols were synthesized from norephedrine and thiophene carbaldehydes (methyl- or ethyl-substituted) and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide -hydroxy nitroalkanols in high conversion (92%). The reaction was optimized in terms of the metal, solvent, temperature and amount of chiral ligand. The corresponding catalyst with Cu(OTf)2 and 2-propanol as the solvent provided the best enantioselectivities (up to 96% ee) of the corresponding nitroalcohols for aliphatic aldehydes. Copyright (c) 2013 John Wiley & Sons, Ltd.
引用
收藏
页码：283 / 289
页数：7
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