Ring-expansion reaction of oximes with aluminum reductants.
The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH(OtBu)3, and (MeOCH2CH2O)2AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.
Graduate School of Science, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan. hcho@mail.pharm.tohoku.ac.jp
Hidetsura
H
Cho
Yusuke
Y
Iwama
Nakako
N
Mitsuhashi
Kenji
K
Sugimoto
Kentaro
K
Okano
Hidetoshi
H
Tokuyama
D017607:Aluminum Compounds / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry*; D019163:Reducing Agents / Q000737:chemistry*
D017607:Aluminum Compounds; D010091:Oximes; D019163:Reducing Agents