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Literature DB >> 16332044

Prevention of undesirable isomerization during olefin metathesis.

Soon Hyeok Hong¹, Daniel P Sanders, Choon Woo Lee, Robert H Grubbs.

Abstract

1,4-Benzoquinones have been found to prevent olefin isomerization of a number of allylic ethers and long-chain aliphatic alkenes during ruthenium-catalyzed olefin metathesis reactions. Electron-deficient benzoquinones are the most effective additives for the prevention of olefin migration. This mild, inexpensive, and effective method to block olefin isomerization increases the synthetic utility of olefin metathesis via improvement of overall product yield and purity.

Entities: Chemical

Year: 2005 PMID： 16332044 DOI： 10.1021/ja052939w

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

62 in total

1. Total synthesis of (-)-tirandamycin C.

Authors: Ming Chen; William R Roush
Journal: Org Lett Date: 2011-12-07 Impact factor: 6.005

2. Indium-mediated allylation of aldehydes, ketones and sulfonimines with 2-(alkoxy)allyl bromides.

Authors: Heemal Dhanjee; Thomas G Minehan
Journal: Tetrahedron Lett Date: 2010-10-20 Impact factor: 2.415

3. Thermally Stable, Latent Olefin Metathesis Catalysts.

Authors: Renee M Thomas; Alexey Fedorov; Benjamin K Keitz; Robert H Grubbs
Journal: Organometallics Date: 2011-12-26 Impact factor: 3.876

4. Halocarbocyclization entry into the oxabicyclo[4.3.1]decyl exomethylene-δ-lactone cores of linearifolin and zaluzanin A: exploiting combinatorial catalysis.

Authors: Sandeep K Ginotra; Jacob A Friest; David B Berkowitz
Journal: Org Lett Date: 2012-02-08 Impact factor: 6.005

10. Synthesis and conformational analysis of locked carbocyclic analogues of 1,3-diazepinone riboside, a high-affinity cytidine deaminase inhibitor.

Authors: Olaf R Ludek; Gottfried K Schroeder; Chenzhong Liao; Pamela L Russ; Richard Wolfenden; Victor E Marquez
Journal: J Org Chem Date: 2009-08-21 Impact factor: 4.354

Prevention of undesirable isomerization during olefin metathesis.

1. Total synthesis of (-)-tirandamycin C.

2. Indium-mediated allylation of aldehydes, ketones and sulfonimines with 2-(alkoxy)allyl bromides.

3. Thermally Stable, Latent Olefin Metathesis Catalysts.

4. Halocarbocyclization entry into the oxabicyclo[4.3.1]decyl exomethylene-δ-lactone cores of linearifolin and zaluzanin A: exploiting combinatorial catalysis.

5. Recent advances in the application of ring-closing metathesis for the synthesis of unsaturated nitrogen heterocycles.

6. Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation.

7. In Search of the Optimal Macrocyclization Site for Neurotensin.

8. Synthesis of fluorinated δ-lactams via cycloisomerization of gem-difluoropropargyl amides.

9. Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.

10. Synthesis and conformational analysis of locked carbocyclic analogues of 1,3-diazepinone riboside, a high-affinity cytidine deaminase inhibitor.