2-Azanorbornane-Based Amino Amide Organocatalysts for Asymmetric Michael Addition of β-Keto Esters with Nitroolefins

Huang Yueming; Rei Togashi; Zubeda Begum; Chigusa Seki; Yuko Okuyama; Eunsang Kwon; Koji Uwai; Michio Tokiwa; Suguru Tokiwa; Mitsuhiro Takeshita; Hiroto Nakano

doi:10.1248/cpb.c25-00296

Regular Article

2-Azanorbornane-Based Amino Amide Organocatalysts for Asymmetric Michael Addition of β-Keto Esters with Nitroolefins

Huang Yueming, Rei Togashi, Zubeda Begum, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano

Author information

Huang Yueming
Graduate School of Engineering, Muroran Institute of Technology, 27–1 Mizumoto, Muroran, Hokkaido 050–8585, Japan
Rei Togashi
Graduate School of Engineering, Muroran Institute of Technology, 27–1 Mizumoto, Muroran, Hokkaido 050–8585, Japan
Zubeda Begum
Graduate School of Engineering, Muroran Institute of Technology, 27–1 Mizumoto, Muroran, Hokkaido 050–8585, Japan
Chigusa Seki
Graduate School of Engineering, Muroran Institute of Technology, 27–1 Mizumoto, Muroran, Hokkaido 050–8585, Japan
Yuko Okuyama
Tohoku Medical and Pharmaceutical University, 4–4–1 Komatsushima, Aoba-Ku, Sendai 981–8558, Japan
Eunsang Kwon
Research and Analytical Center for Giant Molecules, Graduate School of Sciences, Tohoku University, 6–3 Aramaki-Aoba, Aoba-ku, Sendai 980–8578, Japan
Koji Uwai
Graduate School of Engineering, Muroran Institute of Technology, 27–1 Mizumoto, Muroran, Hokkaido 050–8585, Japan
Michio Tokiwa
Tokiwakai Group, 62 Numajiri, Uchigo-Tsudura-machi, Iwaki, Fukushima 973–8053, Japan
Suguru Tokiwa
Tokiwakai Group, 62 Numajiri, Uchigo-Tsudura-machi, Iwaki, Fukushima 973–8053, Japan
Mitsuhiro Takeshita
Tokiwakai Group, 62 Numajiri, Uchigo-Tsudura-machi, Iwaki, Fukushima 973–8053, Japan
Hiroto Nakano Corresponding author
Graduate School of Engineering, Muroran Institute of Technology, 27–1 Mizumoto, Muroran, Hokkaido 050–8585, Japan

Keywords: 2-azanorbornane, organocatalyst, amino amide, asymmetric Michael addition, cage compound

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Supplementary material

2025 Volume 73 Issue 7 Pages 616-620

DOI https://doi.org/10.1248/cpb.c25-00296

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Abstract

Newly designed optically active cage type 2-azanorbornane-based amino amide organocatalysts were developed and employed in the asymmetric Michael addition of β-keto esters with nitroolefins to afford the chiral Michael adducts with good chemical yields (up to 99%) and stereoselectivities (up to diastereomeric ratio (dr) = 97 : 3, up to 96% enantiomeric excess (ee)).

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