Journal
ORGANIC LETTERS
Volume 21, Issue 19, Pages 8132-8137Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03240
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Funding
- China Scholarship Council (CSC)
- CNRS
- MESRI
- Universite Paris-Sud
- ANR [ANR-18-CE07-0033-01]
- Ecole Polytechnique
- Agence Nationale de la Recherche (ANR) [ANR-18-CE07-0033] Funding Source: Agence Nationale de la Recherche (ANR)
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The first examples of a catalytic tandem process involving a ring-closing carbonyl-olefin metathesis and a transfer hydrogenation are described. 1,4-Cyclo-hexadiene has been used as an H-2 surrogate to reduce the cyclic alkenes formed after the metathesis step. The same cationic gallium(III) complex, [IPr center dot GaCl2][SbF6], performs the two steps with functional group tolerance. This stereo selective reaction leads to 1,2-cis-disubstituted cyclopentanes and various cyclohexanes. DFT computations support an unexpected mechanism involving activation of 1,4-cyclo-hexadiene by superelectrophilic gallium(III) dimers.
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