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

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 6 , 2006

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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.

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

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Article Details

VOLUME: 3
ISSUE: 6
Year: 2006
Page: [477 - 483]
Pages: 7
DOI: 10.2174/157017806777828510
Price: $58

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