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.
Oxygenated monoterpenes as dipolarophiles for nitrilimine cycloadditions
L. De Benassuti;L. Garanti;G. Molteni
2004
Abstract
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.Pubblicazioni consigliate
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