2,3-二苯基氮杂环丙烷的区域和立体选择性锂化反应：一项多核核磁共振研究。

Regio- and stereoselective lithiation of 2,3-diphenylaziridines: a multinuclear NMR investigation.

作者信息

Capriati Vito, Florio Saverio, Luisi Renzo, Mazzanti Andrea, Musio Biagia

机构信息

Dipartimento Farmaco-Chimico, Università di Bari, Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi CINMPIS, Via E. Orabona 4, I-70125 - Bari, Italy.

出版信息

J Org Chem. 2008 Apr 18;73(8):3197-204. doi: 10.1021/jo800069k. Epub 2008 Mar 22.

DOI:10.1021/jo800069k

PMID:18358047

Abstract

The alpha-lithiation-trapping sequence of trans-N-alkyl-2,3-diphenylaziridines (s-BuLi or s-BuLi/TMEDA), taking place with a stereochemistry which dramatically depends on the solvent coordinating ability (inversion of configuration in THF and retention in toluene), has been carefully investigated. 1H,13C, and 7Li multinuclear NMR investigations at low temperature suggest that two differently configured lithiated aziridines (monomeric cis-1-Li in THF and dimeric trans-1-Li in toluene) are involved.

摘要

反式-N-烷基-2,3-二苯基氮丙啶的α-锂化-捕获序列（仲丁基锂或仲丁基锂/四甲基乙二胺），其发生的立体化学极大地取决于溶剂的配位能力（在四氢呋喃中构型翻转，在甲苯中构型保持），已得到仔细研究。低温下的1H、13C和7Li多核核磁共振研究表明，涉及两种构型不同的锂化氮丙啶（四氢呋喃中的单体顺式-1-Li和甲苯中的二聚体反式-1-Li）。