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Radical cascades using enantioenriched 7-azabenzonorbornenes and their applications in synthesis

Abstract:

Tandem deoxygenation-neophy-type radical rearrangement-electrophile trapping using xanthates from 7-azabenzonorbornadienes gives 3-exo-substituted 2-aza-5,5-benzonorbornenes, which in some cases undergo isomerisation to (aminomethyl)indenes. The starting xanthates are accessible in good yields and high enantiomeric ratios via asymmetric hydroboration of (aryne/pyrrole-derived) 7-azabenzonorbornadienes. Oxidation (using RuO4) and Birch reduction of the 2-aza-5,6-benzonorbornenes provi...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Publisher's version

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Publisher copy:
10.3762/bjoc.4.38

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Institution:
University of Oxford
Department:
Mathematical,Physical & Life Sciences Division - Chemistry - Chemistry Research Laboratory
Role:
Author
More by this author
Institution:
University of Oxford
Department:
Mathematical,Physical & Life Sciences Division - Chemistry - Chemistry Research Laboratory
Role:
Author
Engineering and Physical Sciences Research Council More from this funder
Publisher:
Beilstein Institut Publisher's website
Journal:
Beilstein Journal of Organic Chemistry Journal website
Volume:
4
Pages:
Article: 38
Publication date:
2008-10-05
DOI:
URN:
uuid:64a8fb92-be7e-4264-ba58-6d609ae17ed8
Local pid:
ora:2771

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