Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 21, Pages 10491-10498Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b00991
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Funding
- National Natural Science Foundation of China [21232003, 21472057, 21572074]
- [201422]
- [CCNU15A02007]
- [2015CFA033]
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Here, we describe a novel [3 + 2] cycloaddition that provides a straightforward approach to pyrroloindolines of 3-substituted indoles with vinyl aziridines and vinyl epoxides and furoindolines bearing vinyl groups (up to 96% yield and 9:1 dr). In contrary to previous reports involving Lewis acid activation, this work reports successful reactions based on the activation of indole using t-BuOK and BEt3 (triethylborane), thereby preserving the free N-H group on indoles. In addition, a gram-scale reaction and a ring-closing metatheis reaction are performed to provide good demonstrations of the synthetic utility of this approach.
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