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Journal article

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

Abstract:

Tandem deoxygenation-neophyl-type radical rearrangement-electrophile trapping using xanthates from 7-azabenzonorbornadienes gives 3-exo-substituted 2-aza-5,6-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 RuO(4)) and Birch reduction of the 2-aza-5,6-benzonorbornenes provide acc...

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Publication status:
Published

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Publisher copy:
10.3762/bjoc.4.38

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Beilstein journal of organic chemistry More from this journal
Volume:
4
Pages:
38
Publication date:
2008-01-01
DOI:
EISSN:
1860-5397
ISSN:
1860-5397
Language:
English
Keywords:
Pubs id:
pubs:34495
UUID:
uuid:6c5c7d69-2540-44fa-824d-126f8e61bec7
Local pid:
pubs:34495
Source identifiers:
34495
Deposit date:
2012-12-19

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