132294-96-3Relevant academic research and scientific papers
Atom-economic synthesis of optically active warfarin anticoagulant over a chiral mof organocatalyst
Shi, Tao,Guo, Zhiwei,Yu, Huixian,Xie, Jianwu,Zhong, Yijun,Zhu, Weidong
, p. 2538 - 2543 (2013)
A novel chiral metal-organic framework (MOF) organocatalyst has been developed, based on readily available MIL-101 and the chiral primary diamine (1R,2R)-1,2-diphenylethylenediamine, by the post-synthetic modification. Over the developed chiral heterogeneous catalyst the asymmetric synthesis of (S)-warfarin with high enantioselectivity can be fulfilled on a gram-scale (2.8 g) with excellent yield (92%) at low cost, making the synthesis method an ideal alternative to existing methods. Copyright
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
