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Enantioselective Cascade Reaction for Synthesis of Quinolinones through Synergistic Catalysis Using Cu–Pybox and Chiral Benzotetramisole as Catalysts
Author(s) -
Lu Xuehe,
Ge Luo,
Cheng Cang,
Chen Jie,
Cao Weiguo,
Wu Xiaoyu
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701741
Subject(s) - enantioselective synthesis , catalysis , chemistry , cascade , vicinal , combinatorial chemistry , aryl , asymmetric induction , cascade reaction , reaction conditions , organic chemistry , chromatography , alkyl
In contrast to the well‐studied asymmetric catalyzed synthesis of tetrahydroquinolines, the asymmetric methodologies toward 3,4‐dihydroquinolin‐2‐ones are quite rare. Herein, the first asymmetric cascade reaction is reported between ethynyl benzoxazinanones and mixed‐anhydrides generated from aryl acetic acids and pivaloyl chloride, based on synergistic catalysis. This allowed the formation of attractive 3,4‐dihydroquinolin‐2‐ones bearing two vicinal chiral centers at C3 and C4 in high yields with excellent diastereo‐ and enantioselectivities. A plausible chiral induction model for this reaction was proposed. The utility of this methodology was exemplified by further elaboration of the cyclization products by removal of the N‐protecting groups.