Synthesis of enantiopure analogues of 3-hydroxyproline and derivatives
- Avenoza, A. 1
- Barriobero, J.I. 1
- Busto, J.H. 1
- Cativiela, C. 2
- Peregrina, J.M. 1
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1
Universidad de La Rioja
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2
Instituto de Nanociencia y Materiales de Aragón
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ISSN: 0957-4166
Argitalpen urtea: 2002
Alea: 13
Zenbakia: 6
Orrialdeak: 625-632
Mota: Artikulua
Beste argitalpen batzuk: Tetrahedron: Asymmetry
Laburpena
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. © 2002 Published by Elsevier Science Ltd.