期刊
CHEMICAL COMMUNICATIONS
卷 56, 期 53, 页码 7265-7268出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc02380a
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资金
- National Natural Science Foundation of China [21602231]
- Natural Science Foundation of Jiangsu Province [BK20191197, BK20181373]
- Major Program of Natural Science Research of Jiangsu Higher Education Institutions of China [18KJA150005]
Despite the widespread use of naphthamide atropisomers in biologically active compounds and asymmetric catalysis, few catalytic methods have succeeded in the enantioselective synthesis of these compounds. Herein, a chiral Bronsted acid (CBA) catalysis strategy was developed for readily scalable dynamic kinetic resolution of challengingortho-formyl naphthamides with pyrrolylanilines. The chiral axis of the atropisomeric amide and a stereogenic center were simultaneously established for a new family of potential biologically active pyrrolopyrazine compounds with high enantio- and diastereoselectivities (up to >20 : 1 d.r. and 98 : 2 e.r.). Epimerization experiments of its derivatives reveal that theN-substitution of the nearby stereogenic center could affect the configurational stability of the axially chiral aromatic amides. These results might be useful for the construction of other kinds of novel axially chiral molecules with a low rotational barrier.
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