Enantioselective direct vinylogous aldol-cyclization cascade reaction between β,γ-unsaturated amides and o-quinones.
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.
A 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.
Yu
Y
Jiang
A 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.
Jun-Hao
JH
Fu
A 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.
Tian-Ze
TZ
Li
A 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.
Feng
F
Sha
A 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.
Xin-Yan
XY
Wu