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

页码：1120 / 1126

页数：7

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