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Literature DB >> 23438063

Chiral cyclopropenyl ketones: reactive and selective Diels-Alder dienophiles.

Laural A Fisher¹, Natalee J Smith, Joseph M Fox.

Abstract

The synthesis and Diels-Alder reactions of cyclopropenyl ketones are described. Cyclopropenyl ketones are highly reactive dienophiles that can engage a range of cyclic dienes and 2,3-dimethylbutadiene. The strategy of using cyclopropenyl ketones to facilitate Diels-Alder reactions is not limited to products that contain three-membered rings, as reductive opening by SmI2 can be used to produce a product that lacks a cyclopropane but retains a quaternary stereogenic center.

Entities: Chemical Gene

Mesh：

Substances：
Cyclopropanes
Ketones

Year: 2013 PMID： 23438063 PMCID： PMC3908886 DOI： 10.1021/jo302683t

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

17 in total

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Authors: J I García; J A Mayoral; L Salvatella
Journal: Acc Chem Res Date: 2000-10 Impact factor: 22.384

2. Gold(I)-catalyzed asymmetric cyclopropenation of internal alkynes.

Authors: John F Briones; Huw M L Davies
Journal: J Am Chem Soc Date: 2012-07-09 Impact factor: 15.419

3. Skeletal diversity construction via a branching synthetic strategy.

Authors: Emma E Wyatt; Suzanne Fergus; Warren R J D Galloway; Andreas Bender; David J Fox; Alleyn T Plowright; Alan S Jessiman; Martin Welch; David R Spring
Journal: Chem Commun (Camb) Date: 2006-07-10 Impact factor: 6.222

4. Studies on the stability of cycloprop-2-ene carboxylate dianions and reactions with electrophiles.

Authors: Laural A Fisher; Joseph M Fox
Journal: J Org Chem Date: 2008-10-14 Impact factor: 4.354

5. Intramolecular Diels-Alder reactions of cyclopropenone ketals.

Authors: Paresma R Patel; Dale L Boger
Journal: Org Lett Date: 2010-08-06 Impact factor: 6.005

6. A Density Functional Theory Study of Secondary Orbital Overlap in Endo Cycloaddition Reactions. An Example of a Diels-Alder Reaction between Butadiene and Cyclopropene.

Authors: Branko S. Jursic
Journal: J Org Chem Date: 1997-05-16 Impact factor: 4.354

7. Endo-exo and facial stereoselectivity in the Diels-Alder reactions of 3-substituted cyclopropenes with butadiene.

Authors: J D Xidos; T L Gosse; E D Burke; R A Poirier; D J Burnell
Journal: J Am Chem Soc Date: 2001-06-13 Impact factor: 15.419

8. Bridged synthons from tetrabromocyclopropene: studies on the rearrangement of the primary Diels-Alder adduct with 2,5-dimethylfuran.

Authors: Ravi S Orugunty; Ion Ghiviriga; Khalil A Abboud; Merle A Battiste; Dennis L Wright
Journal: J Org Chem Date: 2004-01-23 Impact factor: 4.354

9. Intramolecular cyclopropene-furan [2 + 4] cycloaddition followed by a cyclopropylcarbinyl rearrangement to synthesize the BCD rings of cortistatin A.

Authors: Philip Magnus; Ryan Littich
Journal: Org Lett Date: 2009-09-03 Impact factor: 6.005

10. Efficient synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl-5,6-dihydropyran-2-ones via the PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols.

Authors: Xin Cheng; Xuefeng Jiang; Yihua Yu; Shengming Ma
Journal: J Org Chem Date: 2008-10-22 Impact factor: 4.354

3 in total