Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction for the Construction of Bicyclic Skeletons with Multiple Stereocenters by Using a Bifunctional Organocatalytic Strategy: An Efficient Approach to Chiral Macrolides

作者：Jiang, Xianxing; Wang, Long; Kai, Ming; Zhu, Liping; Yao, Xiaojun; Wang, Rui^*

来源：Chemistry - A European Journal, 2012, 18(36): 11465-11473.

DOI：10.1002/chem.201201102

• asymmetric synthesis
• bifunctional catalysts
• enones
• hetero-Diels-Alder reactions
• ketones

We have performed the first bifunctional organocatalytic highly enantio-selective inverse-electron-demand hetero-Diels-Alder reaction of cyclic ketones with enones to afford densely functionalized bicyclic skeletons that contain three stereocenters (up 82% yield, 10:1 d.r., and 97% ee). Unlike the previous IEDDAR catalytic strategy, this method features a double HOMOdienophile/LUMOdiene-activated pathway. Moreover, this process provides a promising method for the construction of enantioenriched macrolides.

• 出版日期2012-9
• 单位兰州大学