期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 17, 期 29, 页码 8202-8208出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201100520
关键词
asymmetric catalysis; cycloaddition; erbium; heterocycles; N,N '-dioxides
资金
- National Natural Science Foundation of China [20732003, 21021001]
- PCSIRT [IRT0846]
- National Basic Research Program of China (973 Program) [2011CB808600]
The asymmetric inverse-electron-demand hetero-Diels-Alder (HDA) reactions of beta,gamma-unsaturated alpha-ketoesters with electron-rich alkenes were investigated, with an N,N'-dioxide/erbium(III) complex employed as the catalyst. Quantitative conversion of the beta,gamma-unsaturated alpha-ketoesters and excellent enantioselectivities (up to > 99% ee) and diastereoselectivities (up to > 99:1 d.r.) were observed for a broad range of substrates by using a 0.5-0.05 mol% catalyst loading under mild reaction conditions. The reaction could be scaled up to the gram scale with the same results. In addition, this was the first application of Er(OTf)(3) to the asymmetric inverse-electron-demand HDA reaction and it behaved as an efficient catalyst. Moreover, the synthetic utility of this methodology was demonstrated with the synthesis of key intermediates of some natural products.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据