期刊
CHEMICAL SCIENCE
卷 11, 期 35, 页码 9386-9394出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc02078h
关键词
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资金
- National Science Foundation MRI Program [CHE-1726652]
- University of North Texas
- NSF [CHE-1464943, CHE-1531468]
A double divergent process has been developed for the reaction of alpha-enaminones with quinones through facile manipulation of catalyst and additive, leading to structurally completely different products. The two divergent processes, which involve formal aza- and oxo-[3 + 2] cycloaddition reactions, are mediated by chiral phosphoric acid and molecular sieves, respectively. While inclusion of phosphoric acid in the reaction switched the reaction pathway to favor the efficient formation of a wide range of N-substituted indoles, addition of 4 angstrom molecular sieves to the reaction switched the reaction pathway again, leading to enantioselective synthesis of 2,3-dihydrobenzofurans in excellent yields and enantioselectivities under mild conditions. Studies in this work suggest that the chiral phosphoric acid acts to lower the transition state energy and promote the formation of amide intermediate for the formal aza-[3 + 2] cycloaddition and the molecular sieves serve to facilitate proton transfer for oxo-[3 + 2] cycloaddition. The reactivity of alpha-enaminones is also disclosed in this work.
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