cheminform abstract: stereoselective synthesis of homochiral annulated sultams via intramolecular...

2001 thiazole derivatives thiazole derivatives R 0260 30 - 135 Stereoselective Synthesis of Homochiral Annulated Sultams via Intramolecular Cycloaddition Reactions. — The aldehydes (I) and (V) are useful precursors of homochiral dipoles which can undergo intramolecular cycloaddition yielding isothiazoloisoxazoles, pyrazoloisothiazoles, and pyrroloisothiazoles. Interestingly, in some cases, racemization takes place. The isoxazole derivative (VIIIa), obtained by cyclization of a nitrile oxide, sponta- neously undergoes aromatization to the fused isoxazole (IX). — (CHIACCHIO, UGO; CORSARO, ANTONINO; RESCIFINA, ANTONIO; BKAITHAN, MAJDI; GRASSI, GIOVANNI; PIPERNO, ANNA; PRIVITERA, TINDARA; ROMEO, GIOVANNI; Tetrahedron 57 (2001) 16, 3425-3433; Dip. Sci. Chim., Univ. Catania, I-95125 Catania, Italy; EN) 1

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Page 1: ChemInform Abstract: Stereoselective Synthesis of Homochiral Annulated Sultams via Intramolecular Cycloaddition Reactions

2001 thiazole derivatives

thiazole derivativesR 0260

30 - 135Stereoselective Synthesis of Homochiral Annulated Sultams viaIntramolecular Cycloaddition Reactions. — The aldehydes (I) and(V) are useful precursors of homochiral dipoles which can undergo intramolec-ular cycloaddition yielding isothiazoloisoxazoles, pyrazoloisothiazoles, andpyrroloisothiazoles. Interestingly, in some cases, racemization takes place. Theisoxazole derivative (VIIIa), obtained by cyclization of a nitrile oxide, sponta-neously undergoes aromatization to the fused isoxazole (IX). — (CHIACCHIO,UGO; CORSARO, ANTONINO; RESCIFINA, ANTONIO; BKAITHAN,MAJDI; GRASSI, GIOVANNI; PIPERNO, ANNA; PRIVITERA, TINDARA;ROMEO, GIOVANNI; Tetrahedron 57 (2001) 16, 3425-3433; Dip. Sci. Chim.,Univ. Catania, I-95125 Catania, Italy; EN)

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