2‐Azanorbornane‐Based Amino Alcohol Organocatalysts for Asymmetric Michael Reaction of β‐Keto Esters with Nitroolefins. Issue 24 (13th June 2019)

• Record Type: Journal Article
• Authors: Togashi, Rei; Chennapuram, Madhu; Seki, Chigusa; Okuyama, Yuko; Kwon, Eunsang; Uwai, Koji; Tokiwa, Michio; Takeshita, Mitsuhiro; Nakano, Hiroto
• Is Part Of: European journal of organic chemistry. Issue 24(2019)
• Page Start: 3882
• Page End: 3889
• Publication Date: 2019-06-13
• Subjects: Organocatalyst -- Amino alcohols -- 2‐Azanorbornane -- Michael addition -- Asymmetric reaction; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201900308
• Languages: English
• ISSNs: 1434-193X

Abstract

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 ). Abstract : A highly enantioselective Michael addition of β‐keto esters to nitroolefins was carried out using newly designed optically active 2‐azanorbornane‐based amino alcohol organocatalysts to produce the corresponding chiral Michael adducts in good chemical yields (up to 99 %) and stereoselectivities (up to dr = 91:9, up to 91 % ee ).