期刊
ORGANIC CHEMISTRY FRONTIERS
卷 8, 期 3, 页码 605-612出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0qo01339k
关键词
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资金
- National Natural Science Foundation of China [21602097, 21601006]
An unprecedented atroposelective annulation method has been developed for the construction of N-heterobiaryl atropisomers, achieving high yields and excellent enantioselectivity. The approach also demonstrates versatility in transforming towards other functional N-heterobiaryl atropisomers.
An unprecedented atroposelective annulation between 2-(tosylamino)aryl ketones and 2-alkynals for the construction of N-heterobiaryl atropisomers is achieved. The reaction involves a Michael/aldol cascade reaction catalyzed by a chiral secondary amine organocatalyst followed by acid promoted aromatization, providing a wide spectrum of axially chiral 4-arylquinoline-3-carbaldehydes in a one-pot fashion in good to high yields (up to 96%) and with excellent enantiocontrol (up to 99% ee). The power of the approach is also demonstrated by versatile transformations towards other functional N-heterobiaryl atropisomers.
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