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Literature DB >> 20586104

From discovery to application: 50 years of the vinylcyclopropane-cyclopentene rearrangement and its impact on the synthesis of natural products.

Tomas Hudlicky¹, Josephine W Reed.

Abstract

Entities: Chemical

Mesh：

Substances：

Year: 2010 PMID： 20586104 DOI： 10.1002/anie.200906001

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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20 in total

1. Cyclopropenes in Metallacycle-Mediated Cross-Coupling with Alkynes: Convergent Synthesis of Highly Substituted Vinylcyclopropanes.

Authors: Natasha F O'Rourke; Glenn C Micalizio
Journal: Org Lett Date: 2016-03-01 Impact factor: 6.005

2. Rhodium-catalyzed ring expansion of cyclopropanes to seven-membered rings by 1,5 C-C bond migration.

Authors: Xiaoxun Li; Min Zhang; Dongxu Shu; Patrick J Robichaux; Suyu Huang; Weiping Tang
Journal: Angew Chem Int Ed Engl Date: 2011-09-09 Impact factor: 15.336

3. Stereospecific ring expansion of chiral vinyl aziridines.

Authors: Matthew Brichacek; Mauricio Navarro Villalobos; Alexandra Plichta; Jon T Njardarson
Journal: Org Lett Date: 2011-02-10 Impact factor: 6.005

4. Effect of protic additives in Cu-catalysed asymmetric Diels-Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids.

Authors: Vincent N G Lindsay; Rebecca A Murphy; Richmond Sarpong
Journal: Chem Commun (Camb) Date: 2017-09-14 Impact factor: 6.222

From discovery to application: 50 years of the vinylcyclopropane-cyclopentene rearrangement and its impact on the synthesis of natural products.

1. Cyclopropenes in Metallacycle-Mediated Cross-Coupling with Alkynes: Convergent Synthesis of Highly Substituted Vinylcyclopropanes.

2. Rhodium-catalyzed ring expansion of cyclopropanes to seven-membered rings by 1,5 C-C bond migration.

3. Stereospecific ring expansion of chiral vinyl aziridines.

4. Effect of protic additives in Cu-catalysed asymmetric Diels-Alder cycloadditions of doubly activated dienophiles: towards the synthesis of magellanine-type Lycopodium alkaloids.

5. Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.

6. Intraannular photoreactions in pseudo-geminally substituted [2.2]paracyclophanes.

Review 7. Recent applications of the divinylcyclopropane-cycloheptadiene rearrangement in organic synthesis.

8. Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes.

9. Formal (4+1)-Cyclization of Ammonium Ylides with Vinylogous para-Quinone Methides.

10. 1,3-Alkyl Transposition in Allylic Alcohols Enabled by Proton-Coupled Electron Transfer.