Enantioselective Nazarov cyclization catalyzed by a cinchona alkaloid derivative. Issue 23 (3rd June 2015)

• Record Type: Journal Article
• Authors: Huang, Yu-Wen; Frontier, Alison J.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 23(2015)
• Page Start: 3523
• Page End: 3526
• Publication Date: 2015-06-03
• Subjects: Nazarov cyclization -- Enantioselective -- Cinchona alkaloid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2014.12.136
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Nucleophilic catalysts for a 1, 6 addition/Nazarov cyclization/elimination sequence were evaluated for their ability to induce enantioselectivity in the electrocyclization step. Of the tertiary amines examined, it was found that a cinchona alkaloid derivative was able to generate substituted 5-hydroxy γ-methylene cyclopentenones with excellent enantioselectivity. The study results suggest that successful cyclization depends upon the ability of the dienyl diketone substrate to readily adopt an s - cis conformation.