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Application of the Russig−Laatsch Reaction to Synthesize a Bis[5]helicene Chiral Pocket for Asymmetric Catalysis
Abstract
The enantiomers of a bis[5]helicenediol ligand ([5]HELOL) have been synthesized in appreciable amounts by a procedure in which key steps are the union of p -benzoquinone with an enol ether of 3-acetylphenanthrene and the displacement of phenol and phenol ether functions by alcohols (the Russig−Laatsch reaction). This diol catalyzes the addition of diethylzinc to aldehydes and gives nonracemic alcohols with enantiomeric excesses as high as 81%. The stereoselectivities and yields are much greater than when the catalyzing diol is BINOL. The enantioselectivities are greater also than those of other reactions catalyzed by helicene ligands.
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Citations
Cites
Enantioselective addition of organozinc reagents to aldehydes
Soai, K., & Niwa, S. (1992) · Chemical Reviews · doi:10.1021/cr00013a004 · Cited by 1,265
Cited by
One hundred years of helicene chemistry. Part 1: non-stereoselective syntheses of carbohelicenes
Gingras, M. (2013) · Chem. Soc. Rev. · doi:10.1039/c2cs35154d · Cited by 802
Kawasaki, T., Suzuki, K., Licandro, E., Bossi, A., Maiorana, S., & Soai, K. (2006) · Tetrahedron: Asymmetry · doi:10.1016/j.tetasy.2006.07.015 · Cited by 82
Matsumoto, A., Yonemitsu, K., Ozaki, H., Míšek, J., Starý, I., Stará, I. G., & Soai, K. (2017) · Organic & Biomolecular Chemistry · doi:10.1039/c6ob02745h · Cited by 45
Metadata
- Authors
- Dreher, S. D., Katz, T. J., Lam, K.-C., & Rheingold, A. L.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-01-16
- Volume
- 65
- Issue
- 3
- Pages
- 815-822
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2001405921
- Cited by
- 187
- References
- 1
- FWCI
- 8.42
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Application of the Russig−Laatsch Reaction to Synthesize a Bis[5]helicene Chiral Pocket for Asymmetric Catalysis. https://app.cochat.ai/papers/10.1021/jo991498u
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- Dreher, S. D., Katz, T. J., Lam, K.-C., & Rheingold, A. L. (2000). Application of the Russig−Laatsch Reaction to Synthesize a Bis[5]helicene Chiral Pocket for Asymmetric Catalysis. The Journal of Organic Chemistry. https://doi.org/10.1021/jo991498u
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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