Palladium-catalyzed decarboxylative cycloaddition of vinylethylene carbonates with formaldehyde: enantioselective construction of tertiary vinylglycols.
An efficient method for the enantioselective construction of tertiary vinylglycols through a palladium-catalyzed asymmetric decarboxylative cycloaddition of vinylethylene carbonates with formaldehyde was developed. By using a palladium complex generated in situ from [Pd2(dba)3]⋅CHCl3 and a phosphoramidite ligand as a catalyst under mild reaction conditions, the process allows conversion of racemic 4-substituted 4-vinyl-1,3-dioxolan-2-ones into the corresponding 1,3-dioxolanes, as methylene acetal protected tertiary vinylglycols, in high yields with good to excellent enantioselectivities.
School of Chemistry and Chemical Engineering, and Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240 (P. R. China).
Ajmal
A
Khan
Renfeng
R
Zheng
Yuhe
Y
Kan
Jiang
J
Ye
Juxiang
J
Xing
Yong Jian
YJ
Zhang
D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D005030:Ethylenes / Q000737:chemistry*; D005557:Formaldehyde / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D002254:Carbonates; D005030:Ethylenes; D014753:Vinyl Compounds; D005557:Formaldehyde; D010165:Palladium; C036216:ethylene
alcohols; asymmetric catalysis; cycloaddition; palladium; synthetic methods