Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 15, Pages 3379-3383Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob00319d
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Funding
- NSFC [22071035]
- One Thousand Young and Middle-Aged College and University Backbone Teachers Cultivation Program of Guangxi
- Student Innovation Training Program [202010602047]
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A variety of tetrahydroquinoline-fused bicycles with multiple stereocenters are synthesized in good yields with high diastereoselectivity through Cu2O-catalyzed [4 + 2] cycloaddition. Mechanistic studies show that the Cu(i) catalyst facilitates the formation of ao-QMs through a radical process and accelerates the [4 + 2] cycloaddition. The reaction can be easily scaled up and the products obtained can be converted into diverse tetrahydroquinoline scaffolds.
A variety of tetrahydroquinoline-fused bicycles bearing multiple stereocenters are prepared in good yields with high diastereoselectivity through Cu2O-catalyzed [4 + 2] cycloaddition of aza-ortho-quinone methides (ao-QMs) with bicyclic alkenes. Mechanistic studies reveal that the Cu(i) catalyst not only promotes the formation of ao-QMs through a radical process by single electron transfer but also accelerates [4 + 2] cycloaddition. The reaction was easily performed on gram scale and the obtained tetrahydroquinoline-fused bicycles can be converted to diverse tetrahydroquinoline scaffolds.
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