钌（II）-菲咯啉催化缺电子烯烃的不对称分子内环丙烷化反应

Ru(II)-Pheox-Catalyzed Asymmetric Intramolecular Cyclopropanation of Electron-Deficient Olefins.

作者信息

Nakagawa Yoko, Chanthamath Soda, Shibatomi Kazutaka, Iwasa Seiji

机构信息

Department of Environmental and Life Sciences, Toyohashi University of Technology, 1-1 Tempaku-cho, Toyohashi, Aichi 441-8580, Japan.

出版信息

Org Lett. 2015 Jun 5;17(11):2792-5. doi: 10.1021/acs.orglett.5b01201. Epub 2015 May 22.

DOI:10.1021/acs.orglett.5b01201

PMID:26000764

Abstract

The first highly enantioselective intramolecular cyclopropanation of electron-deficient olefins, in the presence of Ru(II)--Pheox catalyst, is reported. The corresponding cyclopropane-fused γ-lactones were obtained in high yields (up to 99%) with excellent enantioselectivities (ee up to 99%). Moreover, this method enables efficient access to enantioenriched dicarbonyl cyclopropane derivatives, which are important intermediates for the synthesis of various bioactive compounds.

摘要

据报道，在Ru(II)-Pheox催化剂存在下，实现了缺电子烯烃的首例高对映选择性分子内环丙烷化反应。以高产率（高达99%）和优异的对映选择性（对映体过量高达99%）得到了相应的环丙烷稠合γ-内酯。此外，该方法能够有效合成对映体富集的二羰基环丙烷衍生物，这些衍生物是合成各种生物活性化合物的重要中间体。