Cobalt-catalyzed versus uncatalyzed intramolecular Diels-Alder cycloadditions. Issue 2 (10th January 2018)

• Record Type: Journal Article
• Authors: Biletskyi, Bohdan; Tenaglia, Alphonse; Clavier, Hervé
• Is Part Of: Tetrahedron letters. Volume 59:Issue 2(2018)
• Page Start: 103
• Page End: 107
• Publication Date: 2018-01-10
• Subjects: Cobalt -- Cycloaddition -- Cycloisomerization -- Dienyne -- Carbocycle; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.11.052
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Cobalt-promoted intramolecular [4+2] cycloadditions of dienynes. Important differences as a function of substrates structures have been noticed. Excellent diastereoselectivities were obtained. Abstract: The intramolecular [4+2] cycloadditions of dienynes was investigated using cobalt-based catalysts. Substrates without substitution on alkyne moiety were found to react under thermal activation. The use of a cobalt salt as catalyst made reactions cleaner by limiting the formation of byproducts. Cycloadditions with dienynes possessing a substituent on the alkyne pattern occurred only in presence of a cobalt catalyst which displayed a moderate to good activity depending on the substrate patterns.