Base-controlled selective conversion of Michael adducts of malonates with enones in the presence of iodine.
An efficient base-controlled selective conversion of the Michael adducts of malonates with enones in the presence of iodine is reported. Highly functionalized cyclopropane, oxetane, and α-hydroxylmalonate derivatives are obtained selectively using DBU, Na(2)CO(3), and NaOAc as the base, respectively. O(2) was identified to be crucial to the formation of oxetane and α-hydroxylmalonate derivatives.
School of Petrochemical Engineering, Changzhou University, Changzhou 213164, PR China. estally898@yahoo.com.cn
Chun-Bao
CB
Miao
Min
M
Zhang
Zong-Yong
ZY
Tian
Hai-Tao
HT
Xi
Xiao-Qiang
XQ
Sun
Hai-Tao
HT
Yang
D002254:Carbonates / Q000737:chemistry*; D003521:Cyclopropanes / Q000138:chemical synthesis / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008314:Malonates / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D019346:Sodium Acetate / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry
D002254:Carbonates; D003521:Cyclopropanes; D004988:Ethers, Cyclic; D007659:Ketones; D008314:Malonates; D019346:Sodium Acetate; C005686:sodium carbonate; D014508:Urea; D007455:Iodine; C030797:cyclopropane; C005287:oxetane; C483182:N,N'-dibutylurea