1316231-51-2Relevant academic research and scientific papers
Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes
Chen, Xiang-Yu,Li, Sun,Liu, Qiang,Kumar, Mukesh,Peuronen, Anssi,Rissanen, Kari,Enders, Dieter
supporting information, p. 9735 - 9738 (2018/07/25)
A highly efficient strategy for the kinetic resolution of Michael adducts was realized using a chiral N-heterocyclic carbene catalyst. The kinetic resolution provides a new convenient route to single diastereomers of cyclohexenes and Michael adducts in good yields with high enantiomeric excesses (up to 99 % ee with a selectivity factor of up to 458). This “two flies with one swat” concept allows the synthesis of these two synthetically valuable compound classes at the same time by a single transformation.
Chloramphenicol base chemistry. Part 11: chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones
Yan, Linjie,Wang, Haifeng,Xiong, Fangjun,Tao, Yuan,Wu, Yan,Chen, Fener
, p. 921 - 929 (2017/07/11)
The first chloramphenicol base-derived thiourea-catalyzed enantioselective Michael addition of malononitrile to α,β-unsaturated ketones is reported. The Michael adducts were obtained in good to excellent yields (up to 98% yield) and enantioselectivities (up to 94% ee). This reaction has a broad substrate scope to various α,β-unsaturated ketones. With this in mind, this methodology was successfully applied to the synthesis of a chiral piperidone, an advanced building block for dihydropyridinone P2X7 receptor antagonists.
Organocatalytic Enantioselective Decarboxylative Michael Addition of β-Keto Acids to Dicyanoolefins and Disulfonylolefins
Wei, Yi,Guo, Ran,Dang, Yanfeng,Nie, Jing,Ma, Jun-An
, p. 2721 - 2726 (2016/09/13)
A convenient organocatalytic enantioselective decarboxylative Michael addition of β-keto acids to dicyanoolefins and disulfonylolefins is realized. In the presence of saccharide-derived chiral amino thioureas, the reaction proceeded smoothly to afford a wide range of the Michael adducts in 62–99% yield with 70–94% ee. Moreover, one of the chiral adducts obtained could be readily converted into the monofluorinated product in a total 68% yield over four steps with 85% ee. (Figure presented.).
Squaramide-catalyzed enantioselective Michael addition of malononitrile to chalcones
Yang, Wen,Jia, Yang,Du, Da-Ming
experimental part, p. 332 - 338 (2012/02/04)
A highly enantioselective Michael addition of malononitrile to chalcones catalyzed by a chiral quinine-derived squaramide catalyst has been developed. This organocatalytic reaction at a very low catalyst loading (0.5 mol%) led to chiral γ-cyano carbonyl c
Mesoporous SBA-15 with short mesochannels immobilized natural quinine for asymmetric Michael addition of chalcones
Chen, Qiu,Xin, Cui,Lou, Lan-Lan,Yu, Kai,Ding, Fei,Liu, Shuangxi
experimental part, p. 1378 - 1383 (2012/02/01)
A heterogeneous catalyst of natural quinine supported on the mesoporous SBA-15 of short mesochannels was originally synthesized through a simple co-condensation approach for asymmetric organocatalysed Michael addition of malononitrile to chalcones. The ca
