Article
Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives
Organic Letters
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
6-1-2015
DOI
10.1021/acs.orglett.5b01447
Abstract
Tandem reactions involving Rh-catalyzed intermolecular hydroacylations of alkynes with salicylaldehydes followed by intramolecular oxo-Michael additions are described for the diastereoselective synthesis of 2,3-disubstituted chroman-4-ones. The tandem hydroacylation/oxo-Michael additions occur to form 2,3-disubstituted chroman-4-ones in high yields from a range of 1,2-disubstituted acetylenes and substituted salicylaldehyes. The resulting 2,3-disubstituted chroman-4-ones are readily fluorinated to form trans-3-fluoro-2,3-disubstituted chroman-4-ones in high yields with excellent diastereoselectivity.
Copyright Owner
American Chemical Society
Copyright Date
2015
Language
en
File Format
application/pdf
Citation Information
Xiang-Wei Du and Levi M. Stanley. "Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives" Organic Letters Vol. 17 Iss. 13 (2015) p. 3276 - 3279 Available at: http://works.bepress.com/levi_stanley/3/
Reprinted (adapted) with permission from Organic Letters 17 (2015): 3276, doi:10.1021/acs.orglett.5b01447. Copyright © 2015 American Chemical Society.