2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins

Rei Togashi, Madhu Chennapuram, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

New optically active 2-azanorbornane-based amino alcohol organocatalysts were designed and synthesized, and these catalysts were successfully employed in the asymmetric Michael reaction of β-keto esters with nitroolefins to obtain the corresponding chiral Michael adducts with both high chemical yields (up to 99 %) and high stereoselectivities (up to dr = 91:9, up to 91 % ee).

Original languageEnglish
Pages (from-to)3882-3889
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2019
Issue number24
DOIs
Publication statusPublished - 2019 Jun 30

Keywords

  • 2-Azanorbornane
  • Amino alcohols
  • Asymmetric reaction
  • Michael addition
  • Organocatalyst

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Togashi, R., Chennapuram, M., Seki, C., Okuyama, Y., Kwon, E., Uwai, K., Tokiwa, M., Takeshita, M., & Nakano, H. (2019). 2-Azanorbornane-Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β-Keto Esters with Nitroolefins. European Journal of Organic Chemistry, 2019(24), 3882-3889. https://doi.org/10.1002/ejoc.201900308