Asymmetric One-Pot Four-Component Coupling Reaction: Synthesis of Substituted Tetrahydropyrans Catalyzed by Diphenylprolinol Silyl Ether
Asymmetric One-Pot Four-Component Coupling Reaction: Synthesis of Substituted Tetrahydropyrans Catalyzed by Diphenylprolinol Silyl Ether
复制标题
DOI：
10.1002/anie.201005386
复制
发表时间：
2011-01-01
影响因子：
16.6
通讯作者：
Hayashi, Yujiro
中科院分区：
文献类型：
--
作者：
Ishikawa, Hayato;Sawano, Satoshi;Hayashi, Yujiro
多米诺效应：标题反应使用不对称迈克尔/亨利反应/缩醛化/刘易斯酸介导的烯丙基化反应，以提供具有优异的对映选择性的高度取代的四氢吡喃（参见方案; TMS=三甲基甲硅烷基）。四氢吡喃环中的所有碳原子都被不同的基团取代，五个相邻碳中心的相对和绝对立体化学完全受控。
(Chemical Equation Presented) Domino effect: The title reaction uses an asymmetric Michael/Henry reaction/acetalization/Lewis acid mediated allylation reaction to provide highly substituted tetrahydropyrans with excellent enantioselectivity (see scheme; TMS= trimethylsilyl). All the carbon atoms in the tetrahydropyran ring are substituted with different groups, and the relative and absolute stereochemistry of the five contiguous carbon centers are completely controlled.