Synthesis of alpha-Methylidene-gamma-amino Acid Esters from Aldehydes via an Aminative Umpolung Strategy
文献类型：期刊论文
| 作者 | Xu, Juan1,2; Chen, Jing1,2; Yang, Qin1,2; Ding, Lei1,2; Liu, Xuliang1,2; Xu, Dongfang1,2; Zhao, Baoguo1,2,3 |
| 刊名 | ADVANCED SYNTHESIS & CATALYSIS
 |
| 出版日期 | 2014-10-13 |
| 卷号 | 356期号:14-15页码:3219-3224 |
| 关键词 | Alpha-amino Anions Decarboxylation Morita-baylis-hillman (Mbh) Adducts Umpolung 1 4-diazabicyclo[2.2.2]Octane (Dabco) |
| ISSN号 | 1615-4150 |
| DOI | 10.1002/adsc.201400210 |
| 英文摘要 | This paper describes an efficient method for the synthesis of alpha-methylidene-gamma-amino acid esters from readily available aldehydes by using aminative umpolung strategy. Electrophilic aromatic aldehydes were converted to alpha-imino anions via amination with 2,2-diphenylglycine in methanol and subsequent decarboxylation in acetonitrile. The in situ generated a-imino anions displayed high activity in the reaction with Morita-Baylis-Hillman adducts in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) as catalyst, to give a variety of substituted alpha-methylidene-gamma-amino acid esters in 54-96% yields with 3.2-7.1:1 diastereoselectivity. The resulting alpha-methylidene-gamma-amino acid esters can be efficiently converted into biologically important alpha-exo-methylidene-gamma-lactams under mild conditions. |
| 语种 | 英语 |
| WOS记录号 | WOS:000342906100041 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/51459]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Xu, Dongfang |
| 作者单位 | 1.Shanghai Normal Univ, Educ Minist, Key Lab Resource Chem, Shanghai 200234, Peoples R China 2.Shanghai Normal Univ, Shanghai Key Lab Rare Earth Funct Mat, Shanghai 200234, Peoples R China 3.Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China |
| 推荐引用方式 GB/T 7714 | Xu, Juan,Chen, Jing,Yang, Qin,et al. Synthesis of alpha-Methylidene-gamma-amino Acid Esters from Aldehydes via an Aminative Umpolung Strategy[J]. ADVANCED SYNTHESIS & CATALYSIS,2014,356(14-15):3219-3224. |
| APA | Xu, Juan.,Chen, Jing.,Yang, Qin.,Ding, Lei.,Liu, Xuliang.,...&Zhao, Baoguo.(2014).Synthesis of alpha-Methylidene-gamma-amino Acid Esters from Aldehydes via an Aminative Umpolung Strategy.ADVANCED SYNTHESIS & CATALYSIS,356(14-15),3219-3224. |
| MLA | Xu, Juan,et al."Synthesis of alpha-Methylidene-gamma-amino Acid Esters from Aldehydes via an Aminative Umpolung Strategy".ADVANCED SYNTHESIS & CATALYSIS 356.14-15(2014):3219-3224. |
入库方式： OAI收割
来源：化学研究所
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