644-30-4Relevant articles and documents
Transition-Metal-Free Valorization of Biomass-derived Levulinic Acid Derivatives: Synthesis of Curcumene and Xanthorrhizol
Fu, Yao,Gong, Tian-Jun,Xu, Wen-Yan,Zhuo, Kai-Feng
, p. 884 - 891 (2020/12/13)
Levulinic acid (LA) is acknowledged one of the most promising biomass-derived platform molecules and can be transformed into various value-added chemicals. Here, we report a new reaction process for the valorization of LA derivatives under transition-meta
Tandem Peterson olefination and chemoselective asymmetric hydrogenation of β-hydroxy silanes
Krajangsri, Suppachai,Wu, Haibo,Liu, Jianguo,Rabten, Wangchuk,Singh, Thishana,Andersson, Pher G.
, p. 3649 - 3653 (2019/03/28)
Here, we report the first Ir-N,P complex catalyzed tandem Peterson olefination and asymmetric hydrogenation of β-hydroxy silanes. This reaction resulted in the formation of chiral alkanes in high isolated yields (up to 99%) and excellent enantioselectivity (up to 99% ee) under mild conditions. Modification of the reaction conditions provides a choice to transform either an olefin or the β-hydroxy silane in a chemoselective manner. Additionally, based on this method, an expedient enantioselective synthesis of (S)-(+)-α-curcumene, from a simple ketone, was accomplished in two steps with 75% overall yield and 95% ee.
Stereospecific Hydrogenolysis of Lactones: Application to the Total Syntheses of (R)-ar-Himachalene and (R)-Curcumene
Spielmann, Kim,De Figueiredo, Renata Marcia,Campagne, Jean-Marc
, p. 4737 - 4743 (2017/05/12)
A straightforward strategy for the syntheses of curcumene and ar-himachalene is reported. Synthetic highlights include a catalytic and asymmetric vinylogous Mukaiyama reaction and a stereospecific hydrogenolysis of a tertiary benzylic center using Pd/C or Ni/Raney catalysts. Notably, using Ni/Raney, the stereoselectivity outcome (inversion vs retention) of the hydrogenolysis depends on the tertiary benzylic alcohol substitution.
