Stereoselective cyclopropanation of serine- and threonine-derived oxazines to access new morpholine-based scaffolds |
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Authors: | Sladojevich Filippo Trabocchi Andrea Guarna Antonio |
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Institution: | Department of Organic Chemistry Ugo Schiff, University of Florence, Polo Scientifico e Tecnologico, Via della Lastruccia 13, I-50019, Sesto Fiorentino (FI), Italy. |
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Abstract: | A general strategy for the synthesis of novel, orthogonally protected scaffolds based on the unique 2-oxa-5-azabicyclo4.1.0]heptane structure is presented. The described reaction sequence takes advantage of easily available starting materials such as serine and threonine and leads to stereochemically dense structures in few, high-yielding synthetic steps. We show how the stereochemistry can be easily tuned by starting from different beta-hydroxy-alpha-amino acids and also by means of a transition metal-catalyzed cyclopropanation step. The compounds find application as constrained templates for the construction of geometrically diversified libraries of compounds. |
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