Tertiary amine-promoted enone aziridination: investigations into factors influencing enantioselective induction
Tertiary amine-promoted enone aziridination: investigations into factors influencing enantioselective induction
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DOI：
10.1016/j.tetasy.2013.11.008
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发表时间：
2014-01-15
影响因子：
--
通讯作者：
Scutt, James N.
中科院分区：
文献类型：
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作者：
Armstrong, Alan;Pullin, Robert D. C.;Scutt, James N.
利用原位生成的 N-N 叶立德（胺胺），通过手性叔胺促进的 α,β-不饱和酮的亲核氮丙啶化合成反式-N-未取代的氮丙啶（高达 77% ee）。合成并评估了多种手性叔胺，从而绘制了结构-活性关系。用几种烯酮评估了最有效的不对称氮丙啶化促进剂奎宁，以确定底物结构对产物ee的影响，同时通过X射线晶体学对中间体肼盐进行了表征。 (C) 2013 Elsevier Ltd. 保留所有权利。
trans-N-Unsubstituted aziridines were synthesised (up to 77% ee) via a chiral tertiary amine-promoted nucleophilic aziridination of alpha,beta-unsaturated ketones utilising in situ generated N-N ylides (aminimines). A wide range of chiral tertiary amines were synthesised and evaluated, allowing structure-activity relationships to be drawn. The most efficient promoter for asymmetric aziridination, quinine, was assessed with several enones to ascertain the effect of substrate structure on product ee, while the intermediate hydrazinium salt was characterised by X-ray crystallography. (C) 2013 Elsevier Ltd. All rights reserved.