Stereoselective cyclopropanation of serine- and threonine-derived oxazines to access new morpholine-based scaffolds?

Organic & Biomolecular Chemistry Pub Date: 2008-07-29 DOI: 10.1039/B808895K

Abstract

A general strategy for the synthesis of novel, orthogonally protected scaffolds based on the unique 2-oxa-5-azabicyclo[4.1.0]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 β-hydroxy-α-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.

Graphical abstract: Stereoselective cyclopropanation of serine- and threonine-derived oxazines to access new morpholine-based scaffolds
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