title: Tandem Alkyne Hydroacylation and Oxo-Michael Addition: Diastereoselective Synthesis of 2,3-Disubstituted Chroman-4-ones and Fluorinated Derivatives.
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.
authors.affiliation: Department of Chemistry, Iowa State University, 1605 Gilman Hall, Ames, Iowa 50014, United States.
authors.forename: Xiang-Wei
authors.initials: XW
authors.lastname: Du
authors.affiliation: Department of Chemistry, Iowa State University, 1605 Gilman Hall, Ames, Iowa 50014, United States.
authors.forename: Levi M
authors.initials: LM
authors.lastname: Stanley
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000480:Alkynes; D002867:Chromones; D006845:Hydrocarbons, Fluorinated; C013243:salicylaldehyde; D012238:Rhodium