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Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis.

Publication ,  Journal Article
Malcolmson, SJ; Meek, SJ; Sattely, ES; Schrock, RR; Hoveyda, AH
Published in: Nature
December 2008

Discovery of efficient catalysts is one of the most compelling objectives of modern chemistry. Chiral catalysts are in particularly high demand, as they facilitate synthesis of enantiomerically enriched small molecules that are critical to developments in medicine, biology and materials science. Especially noteworthy are catalysts that promote-with otherwise inaccessible efficiency and selectivity levels-reactions demonstrated to be of great utility in chemical synthesis. Here we report a class of chiral catalysts that initiate alkene metathesis with very high efficiency and enantioselectivity. Such attributes arise from structural fluxionality of the chiral catalysts and the central role that enhanced electronic factors have in the catalytic cycle. The new catalysts have a stereogenic metal centre and carry only monodentate ligands; the molybdenum-based complexes are prepared stereoselectively by a ligand exchange process involving an enantiomerically pure aryloxide, a class of ligands scarcely used in enantioselective catalysis. We demonstrate the application of the new catalysts in an enantioselective synthesis of the Aspidosperma alkaloid, quebrachamine, through an alkene metathesis reaction that cannot be promoted by any of the previously reported chiral catalysts.

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Published In

Nature

DOI

EISSN

1476-4687

ISSN

0028-0836

Publication Date

December 2008

Volume

456

Issue

7224

Start / End Page

933 / 937

Related Subject Headings

  • Stereoisomerism
  • Molybdenum
  • Molecular Structure
  • Ligands
  • Indole Alkaloids
  • General Science & Technology
  • Catalysis
  • Aspidosperma
  • Alkenes
 

Citation

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Malcolmson, S. J., Meek, S. J., Sattely, E. S., Schrock, R. R., & Hoveyda, A. H. (2008). Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis. Nature, 456(7224), 933–937. https://doi.org/10.1038/nature07594
Malcolmson, Steven J., Simon J. Meek, Elizabeth S. Sattely, Richard R. Schrock, and Amir H. Hoveyda. “Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis.Nature 456, no. 7224 (December 2008): 933–37. https://doi.org/10.1038/nature07594.
Malcolmson SJ, Meek SJ, Sattely ES, Schrock RR, Hoveyda AH. Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis. Nature. 2008 Dec;456(7224):933–7.
Malcolmson, Steven J., et al. “Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis.Nature, vol. 456, no. 7224, Dec. 2008, pp. 933–37. Epmc, doi:10.1038/nature07594.
Malcolmson SJ, Meek SJ, Sattely ES, Schrock RR, Hoveyda AH. Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis. Nature. 2008 Dec;456(7224):933–937.
Journal cover image

Published In

Nature

DOI

EISSN

1476-4687

ISSN

0028-0836

Publication Date

December 2008

Volume

456

Issue

7224

Start / End Page

933 / 937

Related Subject Headings

  • Stereoisomerism
  • Molybdenum
  • Molecular Structure
  • Ligands
  • Indole Alkaloids
  • General Science & Technology
  • Catalysis
  • Aspidosperma
  • Alkenes