Remote Enantioselective Friedel–Crafts Alkylations of Furans through HOMO Activation

JL Li, CZ Yue, PQ Chen, YC Xiao…

Index: Li, Jun-Long; Yue, Cai-Zhen; Chen, Peng-Qiao; Xiao, You-Cai; Chen, Ying-Chun Angewandte Chemie - International Edition, 2014 , vol. 53, # 21 p. 5449 - 5452 Angew. Chem., 2014 , vol. 126, # 21 p. 5553 - 5556,4

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Citation Number: 16

Abstract

Abstract Catalytic asymmetric Friedel–Crafts alkylation is a powerful protocol for constructing a chiral C (sp 2)[BOND] C (sp 3) bond. Most previous examples rely on LUMO activation of the electrophiles using chiral catalysts with subsequent attack by electron-rich arenes. Presented herein is an alternative strategy in which the HOMO of the aromatic π system of 2- furfuryl ketones is raised through the formation of a formal trienamine species using a ...