Convenient preparation of aryl-substituted nortropanes by Suzuki-Miyaura methodology1

The synthesis of a new bicyclic vinyl boronate (5) was accomplished from N-Boc-nortropinone (6) in two steps. The Suzuki-Miyaura coupling of 5 to a variety of aryl bromides and inflates afforded 3-aryl-8-azabicyclo[3.2.1]oct-2-enes in good yields by adjusting the substrate and (or) reaction conditio...

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Bibliographic Details
Published inCanadian journal of chemistry Vol. 84; no. 4; p. 555
Main Authors Ghosh, Shyamali, Kinney, William A, Gauthier, Diane A, Lawson, Edward C
Format Journal Article
LanguageEnglish
Published Ottawa Canadian Science Publishing NRC Research Press 01.04.2006
Subjects
Bromides
Chemical reactions
Chemical synthesis
Hydrogenation
Proteins
Research methodology
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Summary:The synthesis of a new bicyclic vinyl boronate (5) was accomplished from N-Boc-nortropinone (6) in two steps. The Suzuki-Miyaura coupling of 5 to a variety of aryl bromides and inflates afforded 3-aryl-8-azabicyclo[3.2.1]oct-2-enes in good yields by adjusting the substrate and (or) reaction conditions. Reduction to the 3-aryl-8-azabicyclo[3.2.1]octanes was achieved by hydrogenation. Interestingly, the coupling was also successful with benzyl bromides, providing entry into another group of intermediates. [PUBLICATION ABSTRACT]
ISSN:0008-4042
1480-3291