111491-45-3Relevant academic research and scientific papers
Stereochemical assignment of 2-amino-1,2,3,4-tetrahydro-1-naphthalenols via oxazolidin-2-one derivatives
Delgado, Antonio,Mauleon, David,Minguillon, Cristina,Feliz, Miguel,Pericas, Miquel A.,Riera, Antoni
, p. 868 - 872 (2007/10/02)
The stereochemical assignment of cis- and trans-2-amino-1,2,3,4-tetrahydro-1-naphthalenols (1) can be performed by means of their conformationally restrained tricyclic tetrahydronaphthooxazol-2-one derivatives 2-6.Thus, 1H and 13C nuclear magnetic resonance data of compounds 2-6 reveal differences between the cis and trans stereoisomers that are independent of the nature and number of the aromatic substituents.Conformational analysis of conpounds 2-6 has been performed from the LAOCOON/3 analysis of their nuclear magnetic resonance spectra and MNDO theoretical results, through the use of the Karplus-Altona equation.Whereas the trans compounds exist in a rigid half-chair conformation, a 1:1 equilibrium of two interconverting half-chair conformers is found for the cis derivatives.
