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.
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]
Enantiopure furo[3,4-c]pyrazole derivatives by intramolecular nitrilimine cycloaddition: a stereoselectivity rationale based upon MP2 calculations
G. Molteni;
2008
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.
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