New asymmetric halo aldol reaction provides a novel approach to biologically important chiral cyclothers and cycloamines.
New asymmetric halo aldol reaction provides a novel approach to biologically important chiral cyclothers and cycloamines.
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新的不对称卤醛醇反应为具有生物学意义的手性环醚和环胺提供了一种新的方法。
DOI：
10.1021/ol049255y
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发表时间：
2004
期刊：
影响因子：
--
通讯作者：
Li,Guigen
中科院分区：
文献类型：
--
作者：
Timmons,Cody;Chen,Dianjun;Cannon,JohnF;Headley,AllanD;Li,Guigen
通过环丙基羰基衍生的烯醇化物与醛反应，发展了一种新的不对称卤代羟醛缩合反应。通过X射线结构分析明确地证实了绝对结构。报道了八个实例，具有良好的产率和高达完全控制的非对映异构体过量。这些卤代羟醛产物在弱碱存在下容易地环化，以良好的产率产生手性2，3-二取代四氢呋喃衍生物，而没有任何观察到的差向异构化。
A new asymmetric halo aldol reaction has been developed by reacting cyclopropyl carbonyl derived enolates with aldehydes. The absolute structure was unambiguously confirmed by X-ray structural analysis. Eight examples were reported with good yields and up to complete control of diastereomeric excesses. These halo aldol products have been readily cyclized in the presence of weak bases to produce chiral 2,3-disubstituted tetrahydrofuran derivatives in good yield without any observed epimerization.