title: First asymmetric synthesis of chiral beta-iodo Baylis-Hillman esters via tandem 1,4-conjugate addition/carbonyl coupling reactions.
abstract: A new asymmetric approach to chiral beta-iodo Baylis-Hillman hydroxy esters was developed via a tandem asymmetric I-C/C-C formation reaction. The reaction was conveniently carried out by slow addition of diethylaluminum iodide into a mixture of aldehyde and alpha,beta-acetylenic menthyl ester in dichloromethane at -23 degrees C. Excellent geometric selectivity, promising diastereoselectivity and modest to high yields (up to 91%) were obtained.
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
authors.forename: Xin
authors.initials: X
authors.lastname: Xu
authors.forename: Dianjun
authors.initials: D
authors.lastname: Chen
authors.forename: Han-Xun
authors.initials: HX
authors.lastname: Wei
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
authors.forename: Tom Ling
authors.initials: TL
authors.lastname: Xiao
authors.forename: Daniel W
authors.initials: DW
authors.lastname: Armstrong
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008752:Methylene Chloride / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D004952:Esters; D008752:Methylene Chloride