Enantioselective synthesis of homoallylic amines through reactions of (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkene-substituted aldimines catalyzed by chiral C1-symmetric NHC-Cu complexes.
Enantioselective synthesis of homoallylic amines through reactions of (pinacolato)allylborons with aryl-, heteroaryl-, alkyl-, or alkene-substituted aldimines catalyzed by chiral C1-symmetric NHC-Cu complexes.
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DOI：
10.1021/ja200311n
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发表时间：
2011-03-16
影响因子：
15
通讯作者：
Hoveyda, Amir H.
中科院分区：
文献类型：
--
作者：
Vieira, Erika M.;Snapper, Marc L.;Hoveyda, Amir H.
本发明公开了一种通过稳定且容易获得的（频哪醇合）烯丙基硼与芳基-、杂芳基-、烷基-或烯基-取代的N-膦酰亚胺的Cu-催化反应对映选择性合成高烯丙基酰胺的催化方法。转化由1-5摩尔%的容易获得的NHC-Cu络合物促进，所述络合物衍生自C1-对称咪唑啉盐，其可以在四个步骤中由市售材料以多克的量制备。烯丙基加成可提供高达定量产率和98.5：1.5对映体比的所需产物，并且适合克级操作。一个机制模型占所观察到的选择性水平和趋势。
A catalytic method for enantioselective synthesis of homoallylamides through Cu-catalyzed reactions of stable and easily accessible (pinacolato)allylborons with aryl-, heteroaryl-,alkyl- or alkenyl-substituted N-phosphinoylimines is disclosed. Transformations are promoted by 1–5 mol % of readily accessible NHC–Cu complexes, derived from C1-symmetric imidazolinium salts, which can be prepared in multi-gram quantities in four steps from commercially available materials. Allyl additions deliver the desired products in up to quantitative yield and 98.5:1.5 enantiomeric ratio and are amenable to gram-scale operations. A mechanistic model accounting for the observed selectivity levels and trends is proposed.
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