Enantioselective Nazarov cyclization catalyzed by a cinchona alkaloid derivative

TETRAHEDRON LETTERS

卷:56

Article

Huang, Yu-Wen¹  Frontier, Alison J.¹ 

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

关键词: Nazarov cyclization;    Enantioselective;    Cinchona alkaloid;   

DOI  :  10.1016/j.tetlet.2014.12.136

来源: Elsevier

【 摘 要 】

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 gamma-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. (C) 2015 Elsevier Ltd. All rights reserved.

【 授权许可】

Free