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

Ruggiu, Agostina A.Lysek, RobertMoreno-Clavijo, ElenaMoreno-Vargas, Antonio J.Robina, InmaculadaVogel, Pierre2011-12-162011-12-162011-12-16201010.1016/j.tet.2010.06.090https://infoscience.epfl.ch/handle/20.500.14299/75211WOS:000281356800010The electrophilic addition of benzeneselenyl chloride to the alkene moiety of 7-azabicyclo[2.2.1]hept-5en-2-yl derivatives has been studied. With camphanates 8 and 9 N-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. (C) 2010 Elsevier Ltd. All rights reserved.7-Azanorbornenes7-Azabicyclo[2.2.1]heptanesNaked sugarHydroxylated prolinesBulgecinineHomoconjugated Carbonyl GroupBulge-Inducing ActivityEnantiomerically PureBacterial MetabolitesFormal SynthesisMytilus-EdulisE-SelectinEpibatidineAnalogsAcidThe 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 prolinestext::journal::journal article::research article