15482-26-5Relevant articles and documents
An efficient method for the synthesis of α-hydroxyalkyl aryl ketones
Chen, Chengqun,Feng, Xinghua,Zhang, Guozhen,Zhao, Qin,Huang, Guosheng
, p. 3205 - 3208 (2008)
Exposure of alkyl aryl ketones to Oxone/trifluoroacetic anhydride in the presence of a catalytic amount of iodobenzene affords α-hydroxyalkyl aryl ketones in good yield. This method provides an effective and economical entry for the installation of α-hydroxy moieties into ketones and should find wide application in the construction of the α-hydroxy ketone subunit in natural product synthesis.
Organocatalytic Synthesis of Substituted Vinylene Carbonates
Onida, Killian,Haddleton, Alice J.,Norsic, Sébastien,Boisson, Christophe,D'Agosto, Franck,Duguet, Nicolas
supporting information, p. 5129 - 5137 (2021/09/18)
The organocatalytic synthesis of substituted vinylene carbonates from benzoins and acyloins was studied using diphenyl carbonate as a carbonyl source. A range of N-Heterocyclic Carbene (NHC) precursors were screened and it was found that imidazolium salts were the most active for this transformation. The reaction occurs at 90 °C under solvent-free conditions. A wide range of substituted vinylene carbonates (symmetrical and unsymmetrical, aromatic or aliphatic), including some derived from natural products, were prepared with 20–99% isolated yields (24 examples). The reaction was also developed using thermomorphic polyethylene-supported organocatalysts as recoverable and recyclable species. The use of such species facilitates the workup and allows the synthesis of vinylene carbonates on the preparative scale (>30 g after 5 runs). (Figure presented.).
Solvent-Free Synthesis of α-Amino Ketones from α-Hydroxyl Ketones via A Novel Tandem Reaction Sequence Based on Heyns Rearrangement
Li, Ling-Yu,Zeng, Qing-Le,Li, Guang-Xun,Tang, Zhuo
supporting information, p. 694 - 699 (2019/03/26)
Heyns rearrangement have been famous for carbohydrate chemists for several decades. However, this reaction was underrated as a useful method for synthetic chemists due to preparative shortcomings. Herein we developed an efficient method for the synthesis of pharmaceutically important α-amino ketones from readily available α-hydroxy ketones and secondary amines through a tandem reaction sequence based on Heyns rearrangement. The reaction smoothly proceeded by using catalytic PTSA as catalyst without solvent. Primary and secondary α-hydroxy ketones were readily used and regioselectively afforded the correspondingly α-amino ketones with moderate yield.