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The regioselectivity of the addition of benzeneselenyl chloride to 7-azanorborn-5-ene-2-yl derivatives is controlled by the 2-substituent: new entry into 3- and 4-hydroxy-5-substituted prolines |
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| Authors: | Agostina A. Ruggiu Elena Moreno-Clavijo Inmaculada Robina |
| Affiliation: | a Institute of Chemical Sciences and Engineering, Laboratory of Glycochemistry and Asymmetric Synthesis, Ecole Polytechnique Fédérale de Lausanne, Batochime, CH-1015 Lausanne, Switzerland b Department of Organic Chemistry, Faculty of Chemistry, University of Seville, P. O. Box 1203, E-41071 Seville, Spain |
| Abstract: | The electrophilic addition of benzeneselenyl chloride to the alkene moiety of 7-azabicyclo[2.2.1]hept-5-en-2-yl derivatives has been studied. With camphanates 8 and 9N-Boc-5-endo-chloro-6-exo-phenylseleno-7-azanorborn-2-yl camphanates 10 and 11 are obtained with high regioselectivity due to a steric control. With N-Boc-7-azanorbor-5-en-2-one (2) the corresponding 6-endo-chloro-5-exo-phenylseleno derivative 15 is obtained in high yield due to a kinetic control attributed to the electron-releasing ability of the homoconjugated carbonyl group. Bicyclic adducts 10 and 11 and 15 are readily converted into 4-hydroxy-(14) and 3-hydroxy-5-substituted proline derivatives 19, respectively. |
| Keywords: | 7-Azanorbornenes 7-Azabicyclo[2.2.1]heptanes Naked sugar Hydroxylated prolines Bulgecinine |
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