title: A sequential indium-mediated aldehyde allylation/palladium-catalyzed cross-coupling reaction in the synthesis of 2-deoxy-beta-C-aryl glycosides.
abstract: Indium-mediated allylation of aldehydes with 2-chloro-3-iodopropene, followed by a palladium-catalyzed cross-coupling reaction with triarylindium reagents or arylboronic acids, leads to aryl-substituted homoallylic alcohols in good to excellent yields and diastereoselectivities. The products obtained from reactions conducted with d-glyceraldehyde acetonide can be transformed into 2-deoxy-beta-C-aryl ribofuranosides in high overall yields. Similarly, 2-deoxy-beta-C-aryl allopyranosides may be prepared efficiently from 2,4-O-benzylidene erythrose.
authors.affiliation: Department of Chemistry and Biochemistry, California State University-Northridge, Northridge, California 91330, USA.
authors.forename: John Alec
authors.initials: JA
authors.lastname: Moral
authors.forename: Seong-Jin
authors.initials: SJ
authors.lastname: Moon
authors.forename: Samuel
authors.initials: S
authors.lastname: Rodriguez-Torres
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Minehan
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006027:Glycosides; D007204:Indium; D010165:Palladium