A highly efficient asymmetric synthesis of optically active alpha, gamma-substituted gamma-butyrolactones using a chiral auxiliary derived from isosorbide.
Using an easily accessible and inexpensive chiral auxiliary derived from isosorbide, optically active alpha,gamma-substituted gamma-butyrolactones were obtained in high enantiomeric purity (up to >99% ee for trans) by the SmI(2)-induced reductive coupling of chiral methacrylate 7 with ketones in the presence of (-)-sultam as a proton source.
Xu
M H
MH
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenlin Lu, Shanghai 200032, P. R. China.
Wang
W
W
Lin
G Q
GQ
D015107:4-Butyrolactone / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007547:Isosorbide / Q000737:chemistry* / Q000378:metabolism*; D007659:Ketones / Q000378:metabolism; D008689:Methacrylates / Q000378:metabolism; D011522:Protons; D013237:Stereoisomerism
D007659:Ketones; D008689:Methacrylates; D011522:Protons; D015107:4-Butyrolactone; D007547:Isosorbide