Enantioselective direct vinylogous aldol-cyclization cascade reaction between β,γ-unsaturated amides and o-quinones
Yu Jiang1, Jun-Hao Fu1, Tian-Ze Li1
1A Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China. xinyanwu@ecust.edu.cn.
Abstract:
1,2-Diketones are employed, for the first time, as electrophiles in the vinylogous aldol reaction. With 5 mol% of chiral tertiary amine-thiourea , a direct vinylogous aldol-cyclization cascade reaction between β,γ-unsaturated amides and o-quinones has been achieved to produce spirocyclic dihydropyranones in 76-99% yield and 82-95% ee.
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