Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 14, Pages 3004-3009Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201905519
Keywords
[2+2+2] cycloaddition; chiral triptycenes; cyclic alkenes; enantioselective synthesis; rhodium
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Funding
- JSPS (Japan) [JP26102004, JP19H00893]
- JSPS [17J08763]
- Umicore
- Grants-in-Aid for Scientific Research [17J08763] Funding Source: KAKEN
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The enantioselective synthesis of distorted pi-extended chiral triptycenes, consisting of three distinct aromatic rings, has been achieved with high ee value of 87 % by the cationic rhodium(I)/segphos complex-catalyzed enantioselective [2+2+2] cycloaddition of 2,2 '-di(prop-1-yn-1-yl)-5,5 '-bis(trifluoromethyl)-1,1 '-biphenyl with 6-methoxy-1,2-dihydronaphthalene followed by the diastereoselective Diels-Alder reaction and aromatization. Demethoxy derivatives were also synthesized by the C-O bond cleavage. In this synthesis, the use of the electron-deficient diyne and the electron-rich alkene is crucial to suppress the undesired strain-relieving carbocation rearrangement and stabilize the distorted triptycene structure.
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