A. M. Gil, E. Buñuel, M. D. Díaz-de-Villegas
Jun 6, 2003
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0
Influential Citations
7
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract Wittig olefinations of methyl (1 S ,2 R ,4 R )- N -benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate with several phosphoranes and the Horner–Wittig reaction, using methyl diethylphosphonoacetate, have been tested in order to evaluate their utility in the synthesis of β-substituted conformationally constrained prolines. Subsequent elaboration of the resulting alkenes has provided proline–amino acid chimeras [combinations of proline with other α-amino acids, such as l -norvaline, l -norleucine, l -α-(3-phenylpropyl)glycine or l -homoglutamic acid] with the 7-azabicyclo[2.2.1]heptane skeleton in an enantiomerically pure form.