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

Title: 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

Volume: 3 Issue: 6

Author(s): Jose Sepulveda-Arques, Ramon Jose Zaragoza, Elena Zaballos-Garcia, Abdelkrim Hamdach, Abdeslem Bentama and Salvador Gil

Affiliation:

Keywords: theoretical studies, aminodiol, oxazinone, oxazolidinone, Silyl migration

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 silyl migration 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.

Cite this article as:

Sepulveda-Arques Jose, Jose Zaragoza Ramon, Zaballos-Garcia Elena, Hamdach Abdelkrim, Bentama Abdeslem and Gil Salvador, 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, Letters in Organic Chemistry 2006; 3 (6) . https://dx.doi.org/10.2174/157017806777828510