132294-97-4Relevant academic research and scientific papers
Highly effective and enantioselective Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones promoted by simple chiral primary amine thiourea bifunctional catalysts
Mei, Ren-Qiang,Xu, Xiao-Ying,Li, Yan-Chun,Fu, Ji-Ya,Huang, Qing-Chun,Wang, Li-Xin
, p. 1566 - 1568 (2011)
Highly asymmetric Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones promoted by chiral primary amine thiourea bifunctional catalysts was developed and a series of Michael adducts were obtained in excellent yields (up to 97%) and enantioselectivities (up to 95% ee). Optically pure S-warfarin was easily obtained in 99% ee after single recrystallization.
Chiral primary amino amide alcohol organocatalyst for the asymmetric Michael addition of 4-hydroxycoumarin with α,β-unsaturated ketones
Kumagai, Jun,Kohari, Yoshihito,Seki, Chigusa,Uwai, Koji,Okuyama, Yuko,Kwon, Eunsang,Nakano, Hiroto
, p. 1124 - 1134 (2015/04/27)
Chiral primary amino amide organocatalysts were designed and synthesized as new organocatalysts for the enantioselective Michael addition of 4-hydroxycoumarin with α,β-unsaturated ketones to produce chiral warfarin (up to 56% ee with up to 92% yield).
Asymmetric synthesis of warfarin and its analogues on water
Rogozińska-Szymczak, Maria,Mlynarski, Jacek
, p. 813 - 820 (2014/06/23)
The asymmetric Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones on water without organic co-solvents is reported to be catalysed by organic primary amines. The application of enantiomerically pure (S,S)-diphenylethylenediamine affords a series of important pharmaceutically active compounds in good to excellent yields (73-98%) and with good enantioselectivities (up to 76% ee) via reactions accelerated by ultrasound. In particular, our developments led to an efficient protocol for the 'solids on water' formation of the anticoagulant warfarin in both enantiomeric forms. The presented scalable and environmentally friendly organocatalytic approach affords the target drug in enantiomerically pure form.
Organocatalytic enantioselective michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones: a simple synthesis of warfarin
Dong, Zhenhua,Wang, Lijia,Chen, Xiaohong,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
experimental part, p. 5192 - 5197 (2010/01/11)
A type of C2-symmetric secondary amine amide catalysts were developed for the asymmetric Michael addition of Ahydroxycoumarin to α,ss-unsaturated ketones. A series of important biologically and pharmaceutically active compounds were obtained in
