Literature DB >> 20386831

Ene reactions between two alkynes? Doors open to thermally induced cycloisomerization of macrocyclic triynes and enediynes.

Iván González1, Anna Pla-Quintana, Anna Roglans, Anna Dachs, Miquel Solà, Teodor Parella, Jordi Farjas, Pere Roura, Vega Lloveras, José Vidal-Gancedo.   

Abstract

A domino process is described combining an ene reaction between two alkynes and a Diels-Alder cycloaddition of the vinylallene formed. The process accounts for the thermally induced cycloisomerization of macrocyclic triynes and enediynes to give fused tetracycles in a stereoselective manner.

Entities:  

Year:  2010        PMID： 20386831     DOI： 10.1039/b926497c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  4 in total

1.  Formal [2 + 2 + 2] cycloaddition strategy based on an intramolecular propargylic ene reaction/Diels-Alder cycloaddition cascade.

Authors:  Julia M Robinson; Takeo Sakai; Katsuhiko Okano; Takafumi Kitawaki; Rick L Danheiser
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

2.  Cyano Diels-Alder and cyano ene reactions. Applications in a formal [2 + 2 + 2] cycloaddition strategy for the synthesis of pyridines.

Authors:  Takeo Sakai; Rick L Danheiser
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

3.  Why nature eschews the concerted [2 + 2 + 2] cycloaddition of a nonconjugated cyanodiyne. Computational study of a pyridine synthesis involving an ene-Diels-Alder-bimolecular hydrogen-transfer mechanism.

Authors:  Yu Lan; Rick L Danheiser; K N Houk
Journal:  J Org Chem       Date:  2012-01-25       Impact factor: 4.354

Review 4.  [2+2+2] cycloaddition reactions of macrocyclic systems catalyzed by transition metals. A review.

Authors:  Anna Pla-Quintana; Anna Roglans
Journal:  Molecules       Date:  2010-12-15       Impact factor: 4.411
  4 in total

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