通过一锅法有机催化迈克尔/亨利/缩酮化反应序列实现高官能化四氢吡喃的不对称合成。
Asymmetric synthesis of highly functionalized tetrahydropyrans via a one-pot organocatalytic Michael/Henry/ketalization sequence.
作者信息
Hahn Robert, Raabe Gerhard, Enders Dieter
机构信息
Institute of Organic Chemistry, RWTH Aachen University , Landoltweg 1, 52074 Aachen, Germany.
出版信息
Org Lett. 2014 Jul 18;16(14):3636-9. doi: 10.1021/ol501236a. Epub 2014 Jun 27.
Abstract
A diastereo- and enantioselective Michael/Henry/ketalization sequence to functionalized tetrahydropyrans is described. The multicomponent cascade reaction uses acetylacetone or β-keto esters, β-nitrostyrenes, and alkynyl aldehydes as substrates affording tetrahydropyrans with five contiguous stereocenters. Employing a bifunctional quinine-based squaramide organocatalyst, the title compounds are obtained in moderate to good yields (27-80%), excellent enantiomeric excesses (93-99% ee), and high diastereomeric ratios (dr > 20:1) after one crystallization.
摘要
描述了一种用于官能化四氢吡喃的非对映和对映选择性迈克尔/亨利/缩酮化序列。该多组分串联反应使用乙酰丙酮或β-酮酯、β-硝基苯乙烯和炔基醛作为底物，得到具有五个连续立体中心的四氢吡喃。使用基于双功能奎宁的方酰胺有机催化剂，经一次结晶后，标题化合物以中等至良好的产率（27-80%）、优异的对映体过量（93-99% ee）和高非对映体比率（dr > 20:1）获得。
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