trans-Cyclooctenes as Chiral Ligands in Rhodium-Catalyzed Asymmetric 1,4-Additions
Tagui Nagano
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, 615-8510 Kyoto, Japan
Search for more papers by this authorShunsuke Einaru
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, 615-8510 Kyoto, Japan
Search for more papers by this authorKenta Shitamichi
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, 615-8510 Kyoto, Japan
Search for more papers by this authorCorresponding Author
Dr. Keisuke Asano
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, 615-8510 Kyoto, Japan
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, Kyoto 615-8510, Japan
E-mail: [email protected]
E-mail: [email protected]
https://smatsubara.wixsite.com/matsubara-kyoto-u/home
Search for more papers by this authorCorresponding Author
Dr. Seijiro Matsubara
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, 615-8510 Kyoto, Japan
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, Kyoto 615-8510, Japan
E-mail: [email protected]
E-mail: [email protected]
https://smatsubara.wixsite.com/matsubara-kyoto-u/home
Search for more papers by this authorTagui Nagano
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, 615-8510 Kyoto, Japan
Search for more papers by this authorShunsuke Einaru
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, 615-8510 Kyoto, Japan
Search for more papers by this authorKenta Shitamichi
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, 615-8510 Kyoto, Japan
Search for more papers by this authorCorresponding Author
Dr. Keisuke Asano
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, 615-8510 Kyoto, Japan
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, Kyoto 615-8510, Japan
E-mail: [email protected]
E-mail: [email protected]
https://smatsubara.wixsite.com/matsubara-kyoto-u/home
Search for more papers by this authorCorresponding Author
Dr. Seijiro Matsubara
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, 615-8510 Kyoto, Japan
Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigaku-katsura, Nishikyo, Kyoto 615-8510, Japan
E-mail: [email protected]
E-mail: [email protected]
https://smatsubara.wixsite.com/matsubara-kyoto-u/home
Search for more papers by this authorGraphical Abstract
trans-Cyclooctenes serve as asymmetric ligands during the rhodium-catalyzed 1,4-additions of organotin reagents to enones. The potentials of these chiral olefins to provide efficient coordination spheres for asymmetric metal catalysis are demonstrated for the first time. These findings provide chiral frameworks for the design of asymmetric ligands for metal catalysts.
Abstract
trans-Cyclooctenes serve as asymmetric ligands for the rhodium-catalyzed 1,4-additions of organotin reagents to enones. We demonstrate, for the first time, that these chiral olefins can provide efficient coordination spheres for asymmetric metal catalysis. As the asymmetric environment around the reaction site is constructed by the trans-cyclooctene framework, the introduction of a substituent at the allylic position further improves enantioselectivity to 93 % ee. These findings provide new chiral framework designs for the asymmetric ligands of metal catalysts.
Supporting Information
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