Journal
ORGANIC LETTERS
Volume 24, Issue 1, Pages 186-190Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03837
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Funding
- National Natural Science Foundation of China [21971105, 21672095]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
- Science and Technology Key Project of Guangdong Province [2020B1111110004]
- Research Projects of Universities of Guangdong Province [2021KCXTD024, 2019KZDXM005]
- Graduate Education Innovation Program of Guangdong Province [2020JGXM100]
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The rhodium-catalyzed bridged (3+2) cycloaddition cascade reactions of N-sulfonyl-1,2,3-triazoles described in this study efficiently allowed the construction of various functionalized bridged ring systems, including the highly strained polycyclic bicyclo[2.2.2]octa[b]indole core of fruticosine.
Here, we describe the rhodium-catalyzed bridged (3+2) cycloaddition cascade reactions of N-sulfonyl-1,2,3-triazoles, which allowed the efficient diastereoselective construction of various functionalized and synthetically challenging bridged ring systems. This simple, direct transformation had a broad substrate scope and excellent functional group tolerance. The highly strained polycyclic bicyclo[2.2.2]octa[b]indole core of fruticosine was synthesized efficiently using this methodology.
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