Efficient conjugate addition of carbonyl compounds to 3-nitro-2H-chromenes in the presence of bases

被引：8

作者：

Hu, Zhi-peng ^{[1
]}

Zhang, Jun-min ^{[1
]}

Lou, Chun-liang ^{[1
]}

Wang, Jin-jia ^{[1
]}

Nie, Shao-zhen ^{[1
]}

Yan, Ming ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Inst Drug Synth & Pharmaceut Proc, Guangzhou 510006, Guangdong, Peoples R China

来源：

ARKIVOC | 2010年

基金：

中国国家自然科学基金;

关键词：

Conjugate addition; carbonyl compounds; 3-nitro-2H-chromenes; organocatalysis; proline; ORGANOCATALYTIC ASYMMETRIC-SYNTHESIS; POTENTIAL ANXIOLYTIC AGENTS; 5-HT1A RECEPTOR LIGANDS; 3-NITROCHROMENE DERIVATIVES; 1,3-DIPOLAR CYCLOADDITIONS; CHROMAN DERIVATIVES; C-NUCLEOPHILES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; 3-NITRO-1,2-DIHYDROQUINOLINES; MOLECULES;

D O I：

10.3998/ark.5550190.0011.a03

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conjugate addition of aldehydes and ketones to 3-nitro-2H-chromenes under basic conditions has been explored. A series of inorganic and organic bases were examined. Proline combined with NaOAc was found to act as an efficient catalyst for the reaction. A number of substituted 3-nitro-2H-chromenes, aldehydes, and ketones are applicable for this transformation. trans-3-Nitro-4-substituted chromanes were sometimes obtained in good yields and with excellent diastereoselectivities. trans-2-Methyl-2-(3-nitrochroman-4-yl) propanal could be transformed into cis-2,3-dihydro-1,1-dimethyl-1H-chroman[3,4-b]pyrrole in one step.

引用

页码：17 / 33

页数：17

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