α-异硫氰酸酯亚胺与活性羰基化合物的有机催化对映选择性串联羟醛缩合-环化反应
Organocatalytic enantioselective tandem aldol-cyclization reaction of α-isothiocyanato imides and activated carbonyl compounds.
作者信息
Guang Jie, Zhao Cong-Gui
机构信息
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas, 78249-0698, USA.
出版信息
Tetrahedron Asymmetry. 2011 Jun 15;22(11):1205-1211. doi: 10.1016/j.tetasy.2011.06.028.
Abstract
The organocatalytic enantioselective tandem aldol-cyclization reactions of α-isothiocyanato imides and activated carbonyl compounds, such as isatins, an α-ketolactone and a 1,2-dione, have been studied with cinchona alkaloid-derived thiourea-catalysts. This methodology provided an easy way to access enantiomerically enriched spirobicyclic thiocarbamates with high yields and good to excellent stereoselectivity, which have been demonstrated to be useful precursors for the synthesis of biologically active molecules.
摘要
使用金鸡纳生物碱衍生的硫脲催化剂，研究了α-异硫氰酸酯亚胺与活化羰基化合物（如异吲哚酮、α-酮内酯和1,2-二酮）的有机催化对映选择性串联羟醛缩合-环化反应。该方法提供了一种简便的途径，能够以高收率和良好至优异的立体选择性获得对映体富集的螺双环硫代氨基甲酸盐，已证明这些化合物是合成生物活性分子的有用前体。
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