A variety of naturally-occurring oxygenated monoterpenes, namely (S)-cis-verbenol, (1R)-(-)-myternol, (1S)-(-)-verbenone, (1R)-(-)-myternal, (S)-(-)-perillyl alcohol, and (S)-(-)-perillaldehyde have been submitted to nitrilimine cycloaddition. These processes were fully regio- and stereoselective for four dipolarophiles. In contrast, regioselective but non-stereoselective cycloadditions occurred in the case of two of the monoterpene derivatives. The configurations of the newly-formed stereocentres of the cycloadducts were assigned on the basis of NOE and NOESY experiments.
Oxygenated monoterpenes as dipolarophiles for nitrilimine cycloadditions / L. De Benassuti, L. Garanti, G. Molteni. - In: TETRAHEDRON. - ISSN 0040-4020. - 60:21(2004), pp. 4627-4633.
Titolo: | Oxygenated monoterpenes as dipolarophiles for nitrilimine cycloadditions |
Autori: | |
Parole Chiave: | 1,3-Dipolar cycloadditions; Monoterpenes; Nitrilimines; Regioselective cycloadditions; Stereoselective cycloadditions |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 2004 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tet.2004.03.077 |
Appare nelle tipologie: | 01 - Articolo su periodico |