Transition-metal-free stereoselective and regioselective hydroamination of 2-benzoylethynyl-4,5,6,7-tetrahydroindoles with amino acids
A new family of unnatural amino acids possessing a tetrahydroindole moiety is obtained by nucleophilic addition of various amino acids to the triple bond of 2-benzoylethynyl-4,5,6,7-tetrahydroindoles. The reaction proceeds chemo-, regio- and stereospecifically in the presence of sodium hydroxide to give the Z-isomeric products in 35-72% yields. Georg Thieme Verlag Stuttgart ? New York.
Sobenina, Lyubov N.,Tomilin, Denis N.,Ushakov, Igor A.,Mikhaleva, Albina I.,Trofimov, Boris A.
experimental part
p. 2084 - 2090
(2012/09/07)
Intramolecular Thermal Oxidoreduction of N-(2-Hydroxypropyl)-β-enaminoesters: Synthesis of N-(Acetonyl)-β-enaminoaldehydes and 2-Acetylpyrroles
Flow pyrolysis of the β-enaminoesters (1) provides the enaminoaldehydes (2), resulting from intramolecular oxidoreduction, and the acetylpyrroles (3); their relative yields depend on the temperature range.