98586-03-9Relevant academic research and scientific papers
Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?
Lang, Qiwei,Yang, Huaxin,Gu, Guoxian,Feng, Qiang,Wen, Jialin,Zhang, Xumu
supporting information, p. 933 - 936 (2021/03/03)
The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.
Isopropylmagnesium chloride-promoted unilateral addition of Grignard reagents to β-diketones: One-pot syntheses of β-tertiary hydroxyl ketones or 3-substituted cyclic-2-enones
Yuan, Rui,Zhao, Dan,Zhang, Li-Yuan,Pan, Xiang,Yang, Yan,Wang, Pei,Li, Hong-Feng,Da, Chao-Shan
supporting information, p. 724 - 728 (2016/01/12)
The regioselective unilateral additions of Grignard reagents to acyclic or cyclic β-diketones were effectively promoted by sub-stoichiometric amounts of i-PrMgCl to afford β-tertiary hydroxyl ketones or 3-substituted cyclic-2-enones, respectively. Also, the addition of Grignard reagents to acyclic β-diketones followed by a reaction with cyclic β-diketones in a one-pot process was put forward. The reaction mechanism was discussed in detail to explain the high regioselectivity via chemical experiments, hydrogen-deuterium exchange and mass spectrometry.
