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Molecules 2010, 15(12), 9230-9251; doi:10.3390/molecules15129230

Review

[2+2+2] Cycloaddition Reactions of Macrocyclic Systems Catalyzed by Transition Metals. A Review

Anna Pla-Quintana and Anna Roglans*

Departament de Química, Universitat de Girona, E-17071-Girona, Spain

* Author to whom correspondence should be addressed.

Received: 24 November 2010; in revised form: 10 December 2010 / Accepted: 14 December 2010 / Published: 15 December 2010

(This article belongs to the Special Issue Cycloaddition Reactions in Organic Synthesis)

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Abstract: Polyalkyne and enediyne azamacrocycles are prepared from arenesulfonamides and various alkyne and alkene derivatives either under basic or neutral conditions. The new family of macrocyclic substrates is tested in the [2+2+2] cycloaddition reaction. Several catalysts are used for the cycloisomerization reaction, and their enantioinduction is evaluated as appropriate. The effect of the structural features of the macrocycles, namely the ring size, substituents in precise positions and the number and type of unsaturations, on the [2+2+2] cycloaddition reaction has also been studied.

Keywords: azamacrocycles; alkynes; alkenes; [2+2+2] cycloadditions; transition metals

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