Title of article :
Reactivity of the Bioactive Aminodiol Subunit: Experimental and Theoretical DFT Study of the Reaction of Silyl Protected Anti-N-Boc-3-Amino-3-Phenyl-1,2-Propanediols with NaH
Author/Authors :
Hamdach, Abdelkrim Universidad de Valencia - Departamento de Química Orgánica, Spain , Bentama, Abdeslem Faculté des Sciences et Techniques - Laboratoire de Chimie Organique, Morocco , Gil, Salvador Universidad de Valencia - Departamento de Química Orgánica, Spain , Zaballos-García, Elena Universidad de Valencia - Departamento de Química Orgánica, Spain , Sepúlveda-Arques, Jose Universidad de Valencia - Departamento de Química Orgánica, Spain , Zaragoza, Ramon Jose Universidad de Valencia - Instituto de Ciencia Molecular - Dpto Q Orgánica, Spain
Abstract :
The reaction of the partially protected (TBDMS), anti-N-Boc-3-methylamino, or anti-N-Boc-3-amino-3-phenyl-1,2-propanediols 7a or 7b, with sodium hydride, yields the oxazolidinones 8 and the silylmigration oxazinones 9, with different ratios (8a:9a; 93:7 and 8b:9b 50:50). The results, have been explained experimental and theoretically by kinetic control of the reaction.
Keywords :
Silyl migration , oxazolidinone , oxazinone , aminodiol , theoretical studies
Journal title :
letters in organic chemistry
Journal title :
letters in organic chemistry
