Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5228814 | Tetrahedron | 2005 | 12 Pages |
Abstract
1,3-Dipolar cycloaddition of acrylamide with the cyclic nitrone derived from proline tert-butyl ester has been employed in the synthesis of bicyclic Gly-(s-cis)Pro isosteres suitably protected for the Fmoc-based solid phase peptide synthesis. (R)-1-Phenylethylamine was introduced as chiral auxiliary to resolve racemic intermediates and obtain enantiopure compounds. Using methacrylamide as dipolarophile, the analogous Ala-Pro mimetics have been prepared in racemic form, whereas the same strategy applied to methyl itaconate failed to give the corresponding Asp-Pro mimetic.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Maria Salvati, Franca M. Cordero, Federica Pisaneschi, Francesca Bucelli, Alberto Brandi,