Radical cascades using enantioenriched 7-azabenzonorbornenes and their applications in synthesis
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...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2008-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.4.38 |
| Summary: | 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 RuO4) and Birch reduction of the 2-aza-5,6-benzonorbornenes provide access to substituted pyrrolidines and tetrahydroindenes, respectively. |
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| ISSN: | 1860-5397 |