Intramolecular Hydride Shift-Mediated Double C(sp3)–H Bond Functionalization of Conformationally Flexible Aliphatic Alkenylidene Malonates
Authors
Sosuke Ando
1
Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Fuchu,
Japan (Ringgold ID: RIN13125)
Masahiro Anada
2
Faculty of Pharmacy, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)
3
Research Institute of Pharmaceutical Sciences, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)
Shunsuke Sueki
2
Faculty of Pharmacy, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)
3
Research Institute of Pharmaceutical Sciences, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)
Kosho Makino
2
Faculty of Pharmacy, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)
3
Research Institute of Pharmaceutical Sciences, Musashino University, Nishitokyo, Japan (Ringgold ID: RIN13214)
Tomoko Kawasaki-Takasuka
4
Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture
and Technology Faculty of Engineering Graduate School of Engineering, Koganei, Japan (Ringgold ID: RIN98293)
4
Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture
and Technology Faculty of Engineering Graduate School of Engineering, Koganei, Japan (Ringgold ID: RIN98293)
We report a double C(sp3)-H bond functionalization from a substrate that has no conformational bias, an indispensable
factor for achieving the sequential hydride shift process. By employing ZnBr2 as a promoter and low concentration conditions (0.025 M), the sequential hydride
shift/cyclization process from an alkenylidene malonate with no substituents on the
linker proceeded smoothly, affording dicyclic piperidine derivatives in moderate to
good chemical yields with excellent diastereoselectivities.
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