1375355-24-0Relevant academic research and scientific papers
Anti-Selective Asymmetric Nitro-Michael Reaction of Furanones: Diastereocontrol by Catalyst
Sekikawa, Tohru,Kitaguchi, Takayuki,Kitaura, Hayato,Minami, Tatsuya,Hatanaka, Yasuo
, p. 646 - 649 (2016)
Catalyst-controlled switching of diastereoselectivity from high syn-selectivity (>98/2 dr, syn) to anti-selectivity (up to 96/4 dr, anti) of the asymmetric nitro-Michael reaction of furanones is described. Anti-diastereoselectivity of the nitro-Michael reaction is very rare. With 0.1-5 mol % loadings of an epi-quinine catalyst, the reaction of 5-substituted 2(3H)-furanones with nitroalkenes smoothly proceeded to give the anti-Michael adducts in good yields (up to 95%) with excellent diastereo- and enantioselectivities (up to 96/4 dr, anti; up to 99% ee). DFT calculations support a model that accounts the high anti-diastereoselectivity. (Chemical Equation Presented).
Catalytic Activity of epi -Quinine-Derived 3,5-Bis(trifluoromethyl)benzamide in Asymmetric Nitro-Michael Reaction of Furanones
Sekikawa, Tohru,Kitaguchi, Takayuki,Kitaura, Hayato,Minami, Tatsuya,Hatanaka, Yasuo
supporting information, p. 3026 - 3029 (2015/06/30)
High catalytic activity of novel epi-quinine-derived 3,5-bis(CF3)benzamide in the asymmetric nitro-Michael reaction is described. With 0.1-5 mol % loadings of this catalyst, the addition of 5-substituted 2(3-H)-furanones to a wide range of nitr
Catalytic enantioselective construction of quaternary stereocenters by direct vinylogous Michael addition of deconjugated butenolides to nitroolefins
Manna, Madhu Sudan,Kumar, Vikas,Mukherjee, Santanu
supporting information; experimental part, p. 5193 - 5195 (2012/06/01)
A direct vinylogous Michael reaction of γ-substituted deconjugated butenolides with nitroolefins has been developed with the help of a newly identified quinine-derived bifunctional catalyst, allowing the synthesis of densely functionalized products with contiguous quaternary and tertiary stereocenters in excellent yield with perfect diastereoselectivity (>20:1 dr) and high enantioselectivity (up to 99:1 er).
