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  • Copper-catalyzed enantioselective Friedel-Crafts alkylation of pyrrole with isatins.

Copper-catalyzed enantioselective Friedel-Crafts alkylation of pyrrole with isatins.

Organic letters (2014-06-10)
Chong Li, Fengfeng Guo, Kun Xu, Sheng Zhang, Yanbin Hu, Zhenggen Zha, Zhiyong Wang
PMID24912009
ABSTRACT

The highly enantioselective Friedel-Crafts alkylation of pyrrole with isatins catalyzed by the tridentate Schiff base/Cu catalyst was developed. Hexafluoroisopropanol (HFIP) was used as a crucial additive to improve the enantioselectivity. In the case of N-unprotected isatins, an innovative substrate slow-releasing strategy was applied by virtue of a Henry/retro-Henry reaction.