Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 27, Pages 11020-11027Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202001794
Keywords
[2+2+2] cycloaddition; alkynes; asymmetric catalysis; circularly polarized luminescence; S-shaped double helicene-like molecules
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Funding
- JSPS (Japan) [26102004, 19H00893, 17H06173]
- CREST from JST (Japan) [JPMJCR19R2]
- HOKUSAI BigWaterfall (RIKEN) [G19012]
- Grants-in-Aid for Scientific Research [19H00893, 17H06173] Funding Source: KAKEN
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An S-shaped double helicene-like molecule (>99 % ee), possessing stable helical chirality, has been synthesized by the rhodium(I)/difluorphos complex-catalyzed highly diastereo- and enantioselective intramolecular double [2+2+2] cycloaddition of a 2-naphthol- and benzene-linked hexayne. The collision between two terminal naphthalene rings destabilizes the helical chirality of the S-shaped double helicene-like molecule, but the introduction of two additional fused benzene rings significantly increases the configurational stability. Thus, no epimerization and racemization were observed even at 100 degrees C. The enantiopure S-shaped double helicene-like molecule forms a trimer through the multiple C-H...pi and C-H...O interactions in the solid-state. The trimers stack to form columnar packing structures, in which neighboring stacks have opposite dipole directions. The accumulation of helical structures in the same direction in the S-shaped double helicene-like molecule enhanced the chiroptical properties.
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