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Modification of Pseudo-C3-Symmetric Trisoxazoline and Its Application to the Friedel-Crafts Alkylation of Indoles and Pyrrole with Alkylidene Malonates

Authors :
Jiao-Long Zhou
Xiu-Li Sun
You-Yun Zhou
Jun-Cheng Zheng
Yong Tang
Ben-Hu Zhu
Source :
Synlett. 2011:935-938
Publication Year :
2011
Publisher :
Georg Thieme Verlag KG, 2011.

Abstract

New pseudo-C3-symmetric hetero-trisoxazoline can be easily prepared on a gram scale in good yield. Its combination with copper(II) triflate exhibits high enantiomeric induction in the asymmetric Friedel-Crafts alkylation between indoles and alkylidene malonates, with up to 97% ee and good to excellent yields. The catalyst loading can be lowered to 0.5 mol% without loss of the enantiomeric excess.

Details

ISSN :
14372096 and 09365214
Volume :
2011
Database :
OpenAIRE
Journal :
Synlett
Accession number :
edsair.doi...........246b3d2a55dbacb581c6a0872b127f3c