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New carbohydrate-based chiral auxiliaries in Diels–Alder reaction

1998; Elsevier BV; Volume: 9; Issue: 15 Linguagem: Inglês

10.1016/s0957-4166(98)00286-9

1362-511X

Maria Lúcia Ferreira, Sérgio Pinheiro, Clarissa C. Perrone, Paulo R. R. Costa, Vı́tor F. Ferreira,

Synthetic Organic Chemistry Methods

The carbohydrate derivatives 1–5 were evaluated as chiral auxiliaries in the Diels–Alder reaction of its acrylate derivatives 6a–e with cyclopentadiene promoted by Lewis acids. Although excellent endo:exo ratios (98:2) were obtained in many cases, the π-facial selectivities were from low to moderate (up to 60% d.e.). An effect of non-coordinating solvents reversing the stereoselectivities of adducts obtained from acrylates 6a,b was also found.