Ni-Catalyzed intramolecular cyclization of Baylis–Hillman adducts of 2-cyanoaniline towards 2,3-dihydroquinolin-4(1H)-ones

Min Yang; Xuanfeng Li; Tingxi Lai; Jian Xiao; Minghui Xu; Bin Chen; Hai-Liang Ni; Bi-Qin Wang; Ping Hu; Peng Cao

doi:10.1039/D5OB00778J

Ni-Catalyzed intramolecular cyclization of Baylis–Hillman adducts of 2-cyanoaniline towards 2,3-dihydroquinolin-4(1H)-ones†

Min Yang,^a Xuanfeng Li,^a Tingxi Lai,^a Jian Xiao,^a Minghui Xu,

*^a Bin Chen,

^a Hai-Liang Ni,^a Bi-Qin Wang,*^a Ping Hu^a and Peng Cao

*^a

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* Corresponding authors

^a College of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610068, China
E-mail: xumh@sicnu.edu.cn, wangbq@sicnu.edu.cn, caopeng@sicnu.edu.cn

Abstract

A Ni-catalyzed reductive cyclization of Baylis–Hillman adducts of 2-cyanoaniline is presented. A novel class of quinolin-4-ones containing a quaternary carbon center were synthesized in moderate to good yields. With ⁱPr-PyBOX as a chiral ligand, the catalytic enantioselective cyclization gave a moderate yield and ee.

Organic & Biomolecular Chemistry

Ni-Catalyzed intramolecular cyclization of Baylis–Hillman adducts of 2-cyanoaniline towards 2,3-dihydroquinolin-4(1H)-ones†

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Ni-Catalyzed intramolecular cyclization of Baylis–Hillman adducts of 2-cyanoaniline towards 2,3-dihydroquinolin-4(1H)-ones

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