Diels-Alder cycloaddition of N-benzyl imine of (1R)-8-phenylmenthyl glyoxylate to cyclopentadiene gave the mixture of adducts 3a-d. Major diastereoisomer, the (1S,exo)-adduct (3a), was isolated in 57% yield and transformed in 74% overall yield into (+)-(1S)-N-benzoyl-2-azabicyclo[2.2.1]heptan-3-one (8). which was compared with an authentic sample of its enantiomer. In the course of this transformation sequence, the chiral auxiliary (1R)-8-phenylmenthol was recovered in 90% yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
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Univ Santiago de Compostela, Fac Farm, Dept Quim Organ, E-15782 Santiago De Compostela, SpainUniv Santiago de Compostela, Fac Farm, Dept Quim Organ, E-15782 Santiago De Compostela, Spain
Garcia-Mera, Xerardo
Rodriguez-Borges, Jose E.
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Univ Porto, Fac Ciencias, CIQ Dept Quim & Bioquim, P-4169007 Oporto, PortugalUniv Santiago de Compostela, Fac Farm, Dept Quim Organ, E-15782 Santiago De Compostela, Spain
Rodriguez-Borges, Jose E.
Vale, M. Luisa C.
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Univ Porto, Fac Ciencias, CIQ Dept Quim & Bioquim, P-4169007 Oporto, PortugalUniv Santiago de Compostela, Fac Farm, Dept Quim Organ, E-15782 Santiago De Compostela, Spain
Vale, M. Luisa C.
Alves, Maria J.
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Univ Minho, Dept Quim, P-4710057 Braga, PortugalUniv Santiago de Compostela, Fac Farm, Dept Quim Organ, E-15782 Santiago De Compostela, Spain