简便的β-二羰基化合物直接不对称α-苯乙炔基化反应  

Convenient Asymmetric Direct α-Phenylethynylation of β-Dicarbonyl Compounds

作　　者：朱敏[1] 李立[1] 孙娜波[1] 李赫[1] 

机构地区：[1]浙江树人大学生物与环境工程学院,杭州310015

出　　处：《高等学校化学学报》2009年第12期2400-2403,共4页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20672100)资助

摘　　要：通过苯乙炔和羟基(+)-10-樟脑磺酰氧基碘苯在氯仿溶剂中反应,合成出一个新的手性炔基芳基碘盐[苯基(苯乙炔基)(10)-樟脑磺酸碘盐].该手性碘盐与β-二羰基化合物的烯醇式负离子在温和条件下易于反应,产物具有中等e.e.值,为β-二羰基化合物在α位不对称引进苯乙炔基提供了一个简单方便的方法.A novel chiral alkynyliodonium salt, phenyl（phenylethynyl）iodonium（10-camphorsulfonate） was prepared by simply stirring of phenylacetylene with [hydroxyl-（（（＋）-10-camphorsulfonyl）oxy）iodo]benzene in CHCl3 overnight at room temperature. The asymmetric reaction with enolate anions of β-dicarbonyl compounds was studied in t-BuOH at room temperature, which gave good yields of α-phenylethynylated products with moderate values of e.e. value. The method for asymmetric direct α-phenylethynylation of β-dicarbonyl compounds was first reported, which had some advantages such as mild reaction conditions, simple procedure and with moderate values of e.e. value. Furthermore, the scope of hypervalent iodine compounds in asymmetric organic synthesis could be extended.

关 键 词：手性有机高价碘盐 苯基(苯乙炔基)(10)-樟脑磺酸碘盐 β-二羰基化合物不对称α-苯乙炔基化反应 

分 类 号：O621.3[理学—有机化学]