A. Avenoza, J. Barriobero, J. H. Busto
Apr 19, 2002
Citations
0
Influential Citations
16
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract All four enantiomerically pure 2-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylic acids, novel restricted analogues of 3-hydroxyproline, are described. The synthesis starts with the Diels–Alder reaction between methyl 2-benzamidoacrylate and Danishefsky's diene and uses as key steps a base-promoted internal nucleophilic displacement of the methanesulfonate group in the cyclohexane ring, followed by a resolution method that involves formation of diastereomers and further separation by crystallization. This synthetic route allowed us to obtain both enantiomers of the N -Boc-7-azabicyclo[2.2.1]heptan-2-ones, valuable ketones used as precursors of (−)- and (+)-epibatidine and other more interesting analogues.