Enantiopure furo[3,4-c]pyrazole derivatives by intramolecular nitrilimine cycloaddition: a stereoselectivity rationale based upon MP2 calculations
Articolo
Data di Pubblicazione:
2008
Citazione:
Enantiopure furo[3,4-c]pyrazole derivatives by intramolecular nitrilimine cycloaddition: a stereoselectivity rationale based upon MP2 calculations / G. Molteni, A. Ponti. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 19:11(2008 Jun 16), pp. 1381-1384. [10.1016/j.tetasy.2008.05.007]
Abstract:
Silver carbonate treatment of hydrazonoyl chloride 4 promoted the in situ generation of the corresponding nitrilimine bearing a stereocentre at the alpha-position of the ethylenic dipolarophile. Intramolecular cycloaddition of the latter intermediate involves the formation of 4-(S)-methyl-6-oxo-3,3a,4,5-tetra hydro-furo[3,4-c]pyrazole derivatives with very good yield and diastereoselectivity. Full rationalization of the experimentally observed stereoselectivity has been pursued by means of MP2 calculations.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
homochiral nitrilimenes; pyrrolo<3,4-C>pyrazole derivates; 1,3-dipolar cycloadditions; imines
Elenco autori:
G. Molteni, A. Ponti
Link alla scheda completa: