一种用于合成固有手性杯[4]芳烃的不对称邻位锂化方法。
An asymmetric ortholithiation approach to inherently chiral calix[4]arenes.
作者信息
Herbert Simon A, Arnott Gareth E
机构信息
Department of Chemistry and Polymer Science, University of Stellenbosch, Matieland 7602, South Africa.
出版信息
Org Lett. 2009 Nov 5;11(21):4986-9. doi: 10.1021/ol902238p.
A general asymmetric synthesis of inherently chiral calix[4]arenes is described: using a chiral oxazoline derived from L-valine, an ortholithiation strategy is employed to give inherently chiral calix[4]arenes with high (93%) enantiomeric excesses. A crystal structure of a phosphine oxide intermediate has been obtained, unambiguously assigning the major diastereomer in the reaction; a mechanism explaining this result is proposed.
本文描述了一种固有手性杯[4]芳烃的通用不对称合成方法：使用由L-缬氨酸衍生的手性恶唑啉，采用邻位锂化策略，得到对映体过量值高（93%）的固有手性杯[4]芳烃。已获得氧化膦中间体的晶体结构，明确确定了反应中的主要非对映异构体；并提出了解释该结果的机理。
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