First asymmetric synthesis of chiral beta-iodo Baylis-Hillman esters via tandem 1,4-conjugate addition/carbonyl coupling reactions.
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.
Xu
Xin
X
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA.
Chen
Dianjun
D
Wei
Han-Xun
HX
Li
Guigen
G
Xiao
Tom Ling
TL
Armstrong
Daniel W
DW
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
D000447:Aldehydes; D004952:Esters; D008752:Methylene Chloride