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reaction of 5-alkoxyfuran-2 5H -ones with nitrone 1 and the reduction of the resulting adducts to give diol 8 both racemic and enantiomerically pure have been reported previously by us in the sequence followed to prepare pyrroloazepines reference 10b
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The reaction of 5-alkoxyfuran-2 (5H) -ones with nitrone 1 and the reduction of the resulting adducts to give diol 8 (both racemic and enantiomerically pure) have been reported previously by us in the sequence followed to prepare pyrroloazepines (reference 10b).
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However, has been reported that 1, 3-dipolar cycloaddition of nitrile oxides to furan-2 5H -ones substituted at the 5-position by sulphur bearing group, afford mixtures of regioisomeric adducts regioselectivity ranging between 64/16 and 84/16. The predominant orientation inthese additions was the same as that observed with 5-alkoxyfuranones. See
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However, has been reported that 1, 3-dipolar cycloaddition of nitrile oxides to furan-2 (5H) -ones substituted at the 5-position by sulphur bearing group, afford mixtures of regioisomeric adducts (regioselectivity ranging between 64/16 and 84/16). The predominant orientation inthese additions was the same as that observed with 5-alkoxyfuranones. See, Alguacil, R.; Fariña, F.; Martín, M. V. Tetrahedron 1996, 52, 3457.
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Feringa has established by AM1 calculus that the cycloaddition of benzonitrile oxide to 5-menthyloxyfuran-2 5H -one is of type I, see reference 14
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Feringa has established by AM1 calculus that the cycloaddition of benzonitrile oxide to 5-menthyloxyfuran-2 (5H) -one is of type I, see reference 14.
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