Simple derivatives of natural amino acids as chiral ligands in the catalytic asymmetric addition of phenylacetylene to aldehydes
Simple derivatives of natural amino acids as chiral ligands in the catalytic asymmetric addition of phenylacetylene to aldehydes
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DOI：
10.1002/ejoc.200400595
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发表时间：
2005-02-25
影响因子：
2.8
通讯作者：
Liu, L
中科院分区：
文献类型：
--
作者：
Han, ZJ;Wang, R;Liu, L
光学活性的丙叉醇是不对称合成中重要的手性构筑单元，而末端炔与醛的不对称加成反应是制备这些手性构筑单元最重要和最有趣的步骤之一。在这项工作中，我们确定了一些简单的(S)-脯氨酸和其他天然氨基酸的衍生物作为手性配体，它们可以与Ti(Oipr)(4)结合，然后用于催化苯乙炔和二乙基锌原位反应生成的乙酰锌与醛的不对称加成反应。Ee值高达90%。(C)Wiley-VCH Verlag GmbH&Co.KGaA，69451，德国温海姆，2005年)。
Optically active propargylic alcohols are important chiral building blocks in asymmetric synthesis, and asymmetric addition of terminal alkynes to aldehydes is one of the most important and interesting procedures by which to prepare these chiral building blocks. In this work we have identified some simple derivatives of (S)-proline and other natural amino acids as chiral ligands that can be combined with Ti(OiPr)(4) and then used to catalyze the asymmetric addition of zinc acetylide, produced in situ by the reaction of phenylacetylene with diethylzinc, to aldehydes. The ee value was as high as 90%. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).