Hydroxylamine catalyzed Nazarov cyclizations of divinyl ketones

Authors

Joseph Z. Hamilton
Nathaniel T. Kadunce
Michael D. McDonald
Laura Rios
Albert Matlin, Oberlin CollegeFollow

Abstract

The first examples of iminium catalyzed Nazarov cyclizations of divinyl ketones are presented. Experiments describing hydroxylamine catalysis of the cyclization of eight alpha-alkoxy divinyl ketones (60-79% yield) and one unactivated divinyl ketone (38% yield) are reported. Phenyl substitution at the beta-position of the divinyl ketone inhibits cyclization, whereas beta-alkyl substituted beta-alkoxy divinyl ketones readily cyclize. (C) 2015 Elsevier Ltd. All rights reserved.

Repository Citation

Hamilton, J.Z., N.T. Kadunce, M.D. McDonald, L. Rios, and A.R. Matlin. 2015. "Hydroxylamine catalyzed Nazarov cyclizations of divinyl ketones." Tetrahedron Letters 56(47): 6622-6624.

Publisher

Elsevier

Publication Date

11-25-2015

Publication Title

Tetrahedron Letters

Department

Chemistry and Biochemistry

Document Type

Article

DOI

10.1016/j.tetlet.2015.10.039

Keywords

Nazarov cyclization, Hydroxylamine catalysis, Iminium ions, Divinyl ketones

Language

English

Format

text