期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 6, 页码 2327-2339出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02838
关键词
-
资金
- National NSF of China [21432005, 21272160, 21321061]
Taking advantage of the coordinating activation strategy, we have developed the cascade oxidative coupling/cyclization of alpha-C(sp(3))-H bonds of amines with enamines or beta-keto esters for the synthesis of three types of five-membered heterocycles. alpha-Amino acids as the substrate lead to 3-amino 1,3-dihydro-2H-pyrrol-2-ones and furan-2(3H)-ones by using air or dioxygen as the sole clean oxidant, respectively. alpha-Amino ketones give a range of 3-amino 1H-pyrroles by using di-test-butyl peroxide as the oxidant. A three-component, one-pot reaction from readily available amine, beta-keto ester, and alpha-amino ketone enhances the practicality of the modular construction of 1H-pyrrole scaffolds. This programmed protocol features simple reaction conditions, readily available starting materials, broad substrate scope, and high functional group tolerance.
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