849417-97-6Relevant academic research and scientific papers
Stereoselective organocatalytic oxidation of alcohols to enals: A homologation method to prepare polyenes
Chen, Xiaobei,Zhang, Yinan,Wan, Huixin,Wang, Wei,Zhang, Shilei
, p. 3532 - 3535 (2016/03/04)
A novel method for organocatalytic oxidation through oxidative enamine catalysis was developed with excellent compatibility for the direct syntheses of enals from simple saturated alcohols. By using this amine-catalyzed IBX-oxidation, a wide range of aromatic and aliphatic substituted enals were successfully generated in high yields and exclusively stereoselective E-geometry. Moreover, varying the solvents and/or the loading amounts of IBX allowed for the selective oxidation of alcohols and aldehydes. Importantly, the homologous application of this method provided a selective and efficient way of preparing various highly sensitive conjugated polyene frameworks, which are enriched in natural products.
Nitrilimine cycloaddition onto 2-azetidinones bearing alkenyl dipolarophile(s)
Del Buttero, Paola,Molteni, Giorgio,Pilati, Tullio
, p. 2413 - 2419 (2007/10/03)
Silver acetate-promoted nitrilimines cycloaddition onto 3(R*)-phenyl-4(R*)-cinnamoyl-2-azetidinone 1 were highly stereoselective giving 4-(4,5-dihydropyrazol-5-yl) carbonyl-2-azetidinones 5 as the major products and regioisomeric 4-(4,5-dihydropyrazol-4-yl) carbonyl-2-azetidinones 6 as the minor one. When the same protocol was applied to the novel 3(R*)-phenyl-4(S*)-(4-benzoyl-E,E-1,3-butadienyl)-2- azetidinone 2 it resulted in site- and regioselective but not stereoselective cycloaddition, involving the formation of the four cycloadducts 10-13.
