Nickel-catalyzed [2 + 2] cycloaddition reaction using bisallenes. Issue 43 (24th October 2019)

• Record Type: Journal Article
• Authors: Arai, Shigeru; Kawata, Yuna; Amako, Yuka; Nishida, Atsushi
• Is Part Of: Tetrahedron letters. Volume 60:Issue 43(2019)
• Publication Date: 2019-10-24
• Subjects: Allenes -- Nickel -- Cycloaddition -- Allenamides; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151168
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Bisallenes are suitable for [2 + 2] cycloaddition under Ni catalysis. Xantphos is the best ligand for bisallene cycloaddition. Allene-allenamides show new reactivity for [2 + 2]–[4 + 2] cycloaddition sequence. The obtained cyclobutanes are suitable for various [4 + 2] cycloaddition. Abstract: A nickel-catalyzed [2 + 2] cycloaddition of bisallenes has been described. Simple bisallenes are employed for the formation of "head to head" cycloadducts in the presence of Ni(0) with xantphos. The dienyl moiety in a product were applicable for various [4 + 2] cycloaddition reactions. Allene-allenamides under Ni-xantphos system gave the tricyclic compounds through sequential [2 + 2]–[4 + 2] cycloaddition reaction in highly stereoselective manner.