Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 24, Pages 12735-12749Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo4023149
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Funding
- University of Ottawa
- Canadian Foundation for Innovation
- Ontario Ministry of Research and Innovation
- NSERC
- Canadian Society for Chemistry
- AstraZeneca Canada
- Boehringer Ingelheim (Canada) Ltd.
- Merck Frosst Canada
- NSERC CGS-M
- NSERC PGS D
- OGS
- FQRNT
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Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.
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