Highly Enantioselective Organocatalytic Conjugate Addition of Nitromethane to Benzylidene Acetones

被引：13
|
作者：
Szanto, Gabor [1 ]
Bombicz, Petra [2 ]
Gruen, Alajos [1 ,3 ]
Kadas, Istvan [1 ]
机构：
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary
[2] Hungarian Acad Sci, Chem Res Ctr, Inst Struct Chem, Dept Xray Diffract, Budapest, Hungary
[3] Budapest Univ Technol & Econ, Hungarian Acad Sci, Organ Chem Technol Res Grp, H-1117 Budapest, Hungary
来源：
CHIRALITY | 2008年 / 20卷 / 10期
关键词：
organocatalyst; Michael addition; enantioselectivity; crystal structure; enantiomer excess;
D O I：
10.1002/chir.20567
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Six active 4-aryl-5-nitro-pentan-2-ones were synthesized enantioselectively from the corresponding 5-aryl-butenones by asymmetric Michael addition of nitromethane using an imidazolidine-type enantioselective organocatalyst. The ee ratio of the products were between 67 and 100%, determined by HPLC with Chiracel OD. Molecular and crystal structure of 3,4-methylenedioxy-phenyl-5-nitro-pentan-2-one has been studied by single crystal X-ray diffraction. Chirality 20:1120-1126, 2008. (C) 2008 Wiley-Liss, Inc.
引用
收藏
页码：1120 / 1126
页数：7
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