通过脯氨醇的对映选择性扩环反应来获得光学活性的 3-叠氮基和 3-氨基哌啶衍生物。
Access to optically active 3-azido- and 3-aminopiperidine derivatives by enantioselective ring expansion of prolinols.
机构信息
Laboratoire de Chimie Organique, ESPCI ParisTech, CNRS (UMR 7084) 10 rue Vauquelin, 75231-Paris Cedex 05, France.
出版信息
Org Lett. 2011 Aug 19;13(16):4442-5. doi: 10.1021/ol201769b. Epub 2011 Jul 27.
PMID:21793544
Abstract
The activation of N-alkyl prolinols by XtalFluor E allowed the formation of an aziridinium intermediate that can react with tetrabutylammonium azide (nBu(4)NN(3)) to produce 3-azidopiperidines and/or 2-(azidomethyl)pyrrolidines, in a ratio up to 100/0. These 3-azidopiperidines can be reduced to the corresponding 3-aminopiperidines.
摘要
XtalFluor E 可以激活 N-烷基脯氨酸，形成氮杂环丁烷中间体，该中间体可以与四丁基叠氮化铵（nBu(4)NN(3)）反应，生成 3-叠氮基哌啶和/或 2-（叠氮甲基）吡咯烷，比例高达 100/0。这些 3-叠氮基哌啶可以还原成相应的 3-氨基哌啶。
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