1201554-54-2Relevant academic research and scientific papers
A sustainable catalytic enantioselective synthesis of norstatine derivatives
Shi, Taoda,Jing, Changcheng,Qian, Yu,Xu, Xinfang,Alavala, Gopi Krishna Reddy,Lv, Xinxin,Hu, Wenhao
supporting information, p. 9792 - 9798 (2019/12/02)
Norstatine derivatives are of important value in pharmaceutical science. However, their catalytic asymmetric synthesis is rare. We developed a sustainable method via chiral phosphoric acid (CPA)-[Rh(OAc)2]2 co-catalyzed multi-component reactions (MCR) of diazoacetates with alcohol/water and imines. This method allows us to synthesize a library of 45 norstatines with excellent enanotioselectivites and broad substrate scope which includes anti-α-aryl-norstatines 11-1, anti-α-alkyl-norstatines 11-2, syn-α-hydro-norstatines 11-3 and syn-α-aryl-norstatines 11-4. The sustainability of this method lies in the reliable scalability, improved safety, and reusable [Rh(OAc)2]2 catalyst. The synthetic value of norstatine derivatives was demonstrated by preparing oxazolinone 14, ezetimibe analogue 15, and Taxol C-13 chain 16. Mechanistic study reveals that the synergetic catalysis of CPA and [Rh(OAc)2]2 is essential to maintain chemo- and enantioselectivity. Control experiments support the mechanism where the reactions proceed through the trapping of hyper-reactive oxonium ylides with imines. Shortly, we report herein the sustainable catalytic enantioselective synthesis of both syn- and anti-norstatine derivatives. We believe that this method might shed light on the sustainable synthesis of norstatine derivative-based drug candidates.
A strategy to synthesize taxol side chain and (-)-epi cytoxazone via chiral Bronsted acid-Rh2(OAc)4 Co-catalyzed enantioselective three-component reactions
Qian, Yu,Xu, Xinfang,Jiang, Liqin,Prajapati, Dipak,Hu, Wenhao
supporting information; experimental part, p. 7483 - 7486 (2011/02/21)
A new approach to synthesize optically active β-amino-α-hydroxyl acid derivatives via chiral Bronsted acid-Rh2(OAc) 4 cocatalyzed three-component reactions of diazo acetates with alcohols and imines is reported. A matched reaction sy
