Articles

Chiral Urea Derivatives Organocatalyzed Asymmetric aza-Friedel-Crafts Reaction of α-Naphthol with N-Tosyl Aldimines

  • Wang Liming ,
  • Lin Geng ,
  • Zhao Meijun ,
  • Liu Dongyao ,
  • Jin Ying
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  • Department of Pharmacy, Jilin Medical University, Jilin 132013

Received date: 2017-08-15

  Revised date: 2017-10-15

  Online published: 2017-11-17

Supported by

Project supported by the National Natural Science Foundation of China (No. 21102055), the Department of Education of Jilin Province (No. JJKH20170409KJ) and the National Students' Program for Innovation and Entrepreneurship Training (No. 201713743010).

Abstract

Chiral urea derivatives as organocatalysts were applied in the asymmetric aza-Friedel-Crafts reaction of α-naphthol with 14 N-tosyl aldimines. The desired chiral aminoarylnaphthols were obtained in 70%~86% yields with up to 78% enantiomeric excess (ee) under the screened optimal condition. The catalyst type and the substrate scope were broadened in this methodology.

Cite this article

Wang Liming , Lin Geng , Zhao Meijun , Liu Dongyao , Jin Ying . Chiral Urea Derivatives Organocatalyzed Asymmetric aza-Friedel-Crafts Reaction of α-Naphthol with N-Tosyl Aldimines[J]. Chinese Journal of Organic Chemistry, 2018 , 38(3) : 642 -647 . DOI: 10.6023/cjoc201708028

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