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Literature DB >> 19053484

Stereoselective, dual-mode ruthenium-catalyzed ring expansion of alkynylcyclopropanols.

Abstract

A novel, dual-pathway ring expansion of alkynylcyclopropanols is described. On treatment with a ruthenium catalyst, these compounds undergo highly selective enlargement to either (Z)-alkylidene cyclobutanones or beta-substituted cyclopentenones. The unique ability to access the least selective double bond isomers of alkylidene cyclobutanones and the dramatic shift of reactivity observed further illustrate the particular intricacies of ruthenium catalysis when compared to other alkynophilic transition metals.

Entities: CellLine Chemical

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Year: 2008 PMID： 19053484 PMCID： PMC2655345 DOI： 10.1021/ja807894t

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

14 in total

1. A catalytic asymmetric Wagner-Meerwein shift.

Authors: B M Trost; T Yasukata
Journal: J Am Chem Soc Date: 2001-07-25 Impact factor: 15.419

2. Synthesis of 2-alkylidenecyclopentanones via palladium-catalyzed cross-coupling of 1-(1-Alkynyl)cyclobutanols and aryl or vinylic halides

Authors:
Journal: Org Lett Date: 2000-10-19 Impact factor: 6.005

3. An alkyne strategy for the asymmetric synthesis of natural products: application to (+)-spirolaxine methyl ether.

Authors: Barry M Trost; Andrew H Weiss
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Palladium-catalyzed diastereo- and enantioselective Wagner-Meerwein shift: control of absolute stereochemistry in the C-C bond migration event.

Authors: Barry M Trost; Jia Xie
Journal: J Am Chem Soc Date: 2008-04-23 Impact factor: 15.419

5. The atom economy--a search for synthetic efficiency.

Authors: B M Trost
Journal: Science Date: 1991-12-06 Impact factor: 47.728

6. Facile palladium(0)-catalyzed ring expansion reactions of hydroxy methoxyallenyl cyclic compounds via hydropalladation.

Authors: Yoshimitsu Nagao; Akiharu Ueki; Kazunori Asano; Satoru Tanaka; Shigeki Sano; Motoo Shiro
Journal: Org Lett Date: 2002-02-07 Impact factor: 6.005

7. An alkyne hydrosilylation-oxidation strategy for the selective installation of oxygen functionality.

Authors: Barry M Trost; Zachary T Ball; Kai M Laemmerhold
Journal: J Am Chem Soc Date: 2005-07-20 Impact factor: 15.419

8. Synthesis of 2-alkylidenecyclopentanones via palladium-catalyzed carbopalladation/ring expansion of 1-(1-alkynyl)cyclobutanols.

Authors: Richard C Larock; Ch Kishan Reddy
Journal: J Org Chem Date: 2002-04-05 Impact factor: 4.354

9. An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes.

Authors: Barry M Trost; Robert C Livingston
Journal: J Am Chem Soc Date: 2008-08-15 Impact factor: 15.419

10. Palladium-catalyzed ring expansion reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. stereospecific synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones.

Authors: Masahiro Yoshida; Kenji Sugimoto; Masataka Ihara
Journal: Org Lett Date: 2004-06-10 Impact factor: 6.005

7 in total

Stereoselective, dual-mode ruthenium-catalyzed ring expansion of alkynylcyclopropanols.

1. A catalytic asymmetric Wagner-Meerwein shift.

2. Synthesis of 2-alkylidenecyclopentanones via palladium-catalyzed cross-coupling of 1-(1-Alkynyl)cyclobutanols and aryl or vinylic halides

3. An alkyne strategy for the asymmetric synthesis of natural products: application to (+)-spirolaxine methyl ether.

4. Palladium-catalyzed diastereo- and enantioselective Wagner-Meerwein shift: control of absolute stereochemistry in the C-C bond migration event.

5. The atom economy--a search for synthetic efficiency.

6. Facile palladium(0)-catalyzed ring expansion reactions of hydroxy methoxyallenyl cyclic compounds via hydropalladation.

7. An alkyne hydrosilylation-oxidation strategy for the selective installation of oxygen functionality.

8. Synthesis of 2-alkylidenecyclopentanones via palladium-catalyzed carbopalladation/ring expansion of 1-(1-alkynyl)cyclobutanols.

9. An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes.

10. Palladium-catalyzed ring expansion reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. stereospecific synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones.

1. A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions.

Review 2. Indenylmetal Catalysis in Organic Synthesis.

3. Tandem ruthenium-catalyzed redox isomerization--O-conjugate addition: an atom-economic synthesis of cyclic ethers.

4. Gold(I)-catalyzed enantioselective ring expansion of allenylcyclopropanols.

5. Rh-catalyzed Reagent-Free Ring Expansion of Cyclobutenones and Benzocyclobutenones.

6. Divergent ring-opening coupling between cyclopropanols and alkynes under cobalt catalysis.

7. Rh(II)-Catalyzed Alkynylcyclopropanation of Alkenes by Decarbenation of Alkynylcycloheptatrienes.