二碘化钐介导的非对映选择性共轭还原反应：(2S,3R)-N-乙酰基-2-氨基-2,3-二氘代-3-苯基丙酸甲酯的不对称合成
Diastereoselective conjugate reduction with samarium diiodide: asymmetric synthesis of methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate.
作者信息
Davies Stephen G, Rodríguez-Solla Humberto, Tamayo Juan A, Garner A Christopher, Smith Andrew D
机构信息
The Department of Organic Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK OX1 3TA.
出版信息
Chem Commun (Camb). 2004 Nov 7(21):2502-3. doi: 10.1039/b408257e. Epub 2004 Sep 8.
DOI:10.1039/b408257e
PMID:15514836
Abstract
A highly diastereoselective conjugate reduction using SmI2 and D2O has been demonstrated on a homochiral benzylidene diketopiperazine template, giving methyl (2S,3R)-N-acetyl-2-amino-2,3-dideuterio-3-phenylpropionate in 93% de and 90% ee after deprotection, hydrolysis and N-acetylation.
摘要
已证明在同手性亚苄基二酮哌嗪模板上使用SmI2和D2O进行高度非对映选择性共轭还原，在脱保护、水解和N-乙酰化后，得到甲基(2S,3R)-N-乙酰基-2-氨基-2,3-二氘代-3-苯基丙酸酯，氘代率为93%，对映体过量率为90%。
Zotero 插件