64869-25-6Relevant articles and documents
-
Heathcock,C.H. et al.
, p. 7077 - 7079 (1979)
-
-
Buse,C.T.,Heathcock,C.H.
, p. 8109 - 8110 (1977)
-
MNBA-mediated β-lactone formation: Mechanistic studies and application for the asymmetric total synthesis of tetrahydrolipstatin
Shiina, Isamu,Umezaki, Yuma,Kuroda, Nobutaka,Iizumi, Takashi,Nagai, Shunsuke,Katoh, Takashi
experimental part, p. 4885 - 4901 (2012/07/30)
Various β-lactones were prepared from β-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.
Synthesis of 2-Arylethylamines by the Curtius Rearrangement
Schulze, Matthias
experimental part, p. 1461 - 1476 (2010/07/08)
2-Arylethylamine derivatives were synthesized using the Curtius reaction and with three different methods of preparing the acyl azide functional group. Carbamates derived from isocyanate were convenient protecting groups for alkylation of amines. Starting from benzaldehyde, amphetamine was prepared in three steps through an oxazolidin-2-one intermediate in 62% overall yield. Copyright Taylor & Francis Group, LLC.