1453496-06-4

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 17428-96-5 1,1-d2-3-phenylpropan-1-ol 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 104-53-0 3-phenyl-propionaldehyde 
• 1184844-25-4 (E)-4,4,4-trifluoro-1-(4-methoxyphenyl)-2-buten-1-one 
• 1453496-20-2 1-oxo-3-phenyl(1-²H)propan-2-yl 4-nitrobenzoate 
• 1262801-38-6 1-oxo-3-phenylpropan-2-yl p-nitrobenzoate 
• 264279-00-7 4,4,4-trifluoro-1-(4-methoxyphenyl)-2-butyn-1-ol 

Relevant academic research and scientific papers

Stereospecific asymmetric N-heterocyclic carbene (NHC)-catalyzed redox synthesis of trifluoromethyl dihydropyranones and mechanistic insights

N-Heterocyclic carbene (NHC)-catalyzed redox asymmetric hetero-Diels-Alder reactions of α-aroyloxyaldehydes with β-trifluoromethyl enones generates synthetically useful dihydropyranones containing a stereogenic trifluoromethyl substituent in good yields (up to 81%) and excellent diastereoselectivity and enantioselectivity (up to >95:5 dr and >99% ee). The process is stereospecific, with use of either (E)- or (Z)-β- trifluoromethyl enones forming syn- or anti-dihydropyranone products, respectively. Mechanistic studies through in situ kinetic analysis of the reaction reveal key differences in reactivity between chiral NHC precursor 1 and an achiral NHC precursor.