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Literature DB >> 22132946

A ring fragmentation approach to medium-sized cyclic 2-alkynones.

Nikolay P Tsvetkov¹, Ali Bayir, Samuel Schneider, Matthias Brewer.

Abstract

Bicyclic γ-silyloxy-β-hydroxy-α-diazoketones, in which the Cβ-Cγ bond is the ring fusion bond, productively fragment when treated with tin(IV) chloride to provide medium-sized cyclic 2-alkynones. This method provides good to excellent yields of 10-, 11-, and 12-membered alkynone products.

Entities: Chemical

Mesh：

Substances：
Cycloparaffins

Year: 2011 PMID： 22132946 PMCID： PMC3253231 DOI： 10.1021/ol2030422

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

7 in total

1. Metal-mediated synthesis of medium-sized rings.

Authors: L Yet
Journal: Chem Rev Date: 2000-08-09 Impact factor: 60.622

2. Regioselective cross-metathesis reaction induced by steric hindrance.

Authors: Samir BouzBouz; Rebecca Simmons; Janine Cossy
Journal: Org Lett Date: 2004-09-30 Impact factor: 6.005

3. Lewis acid promoted carbon-carbon bond cleavage of gamma-silyloxy-beta-hydroxy-alpha-diazoesters.

Authors: Cristian Draghici; Matthias Brewer
Journal: J Am Chem Soc Date: 2008-03-06 Impact factor: 15.419

4. Generation of medium-ring cycloalkynes by ring expansion of vinylogous acyl triflates.

Authors: Jumreang Tummatorn; Gregory B Dudley
Journal: Org Lett Date: 2011-02-24 Impact factor: 6.005

5. Preparation of tethered aldehyde ynoates and ynones by ring fragmentation of cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls.

Authors: Ali Bayir; Cristian Draghici; Matthias Brewer
Journal: J Org Chem Date: 2010-01-15 Impact factor: 4.354

6. Highly stereoselective approach to alk-2-yne-1,4-diols by oxazaborolidine-mediated reduction of alk-2-yne-1,4-diones.

Authors: Xavier Ariza; Jordi Bach; Ramon Berenguer; Jaume Farràs; Montserrat Fontes; Jordi Garcia; Marta López; Jordi Ortiz
Journal: J Org Chem Date: 2004-08-06 Impact factor: 4.354

7. Synthesis of fused oxabicyclic systems by metal-catalyzed intramolecular addition of 1,3-cycloalkyldiones to alkynes.

Authors: Moisés Gulías; J Ramón Rodríguez; Luis Castedo; José L Mascareñas
Journal: Org Lett Date: 2003-05-29 Impact factor: 6.005

7 in total

4 in total

A ring fragmentation approach to medium-sized cyclic 2-alkynones.

1. Metal-mediated synthesis of medium-sized rings.

2. Regioselective cross-metathesis reaction induced by steric hindrance.

3. Lewis acid promoted carbon-carbon bond cleavage of gamma-silyloxy-beta-hydroxy-alpha-diazoesters.

4. Generation of medium-ring cycloalkynes by ring expansion of vinylogous acyl triflates.

5. Preparation of tethered aldehyde ynoates and ynones by ring fragmentation of cyclic gamma-oxy-beta-hydroxy-alpha-diazo carbonyls.

6. Highly stereoselective approach to alk-2-yne-1,4-diols by oxazaborolidine-mediated reduction of alk-2-yne-1,4-diones.

7. Synthesis of fused oxabicyclic systems by metal-catalyzed intramolecular addition of 1,3-cycloalkyldiones to alkynes.

1. Migratory Aptitudes in Rearrangements of Destabilized Vinyl Cations.

2. Fragmentation of bicyclic γ-silyloxy-β-hydroxy-α-diazolactones as an approach to ynolides.

3. Remote C-H insertion of vinyl cations leading to cyclopentenones.

Review 4. Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds.