Alpha-amidation of cyclic ethers catalyzed by simple copper salt and a mild and efficient preparation method for alpha,omega-amino alcohols.
Copper(II) trifluoromethanesulfonate catalyzed the amidation of cyclic ethers with iminoiodanes under mild conditions (CH2Cl2, 40 degrees C) with good yields (up to 86% based on 97% conversion) and selectivity (only alpha-amino products were found). Subsequently, the tosylamidated products could undergo a reductive ring-opening reaction to give alpha,omega-amino alcohols.
He
Ling
L
Department of Chemistry, Key Laboratory of Green Chemistry and Technology, Ministry of Education, Sichuan University, Chengdu, People's Republic of China.
Yu
Jing
J
Zhang
Ji
J
Yu
Xiao-Qi
XQ
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004988:Ethers, Cyclic / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D000605:Amino Alcohols; D004988:Ethers, Cyclic; D009942:Organometallic Compounds; C464593:copper(II) trifluoromethanesulfonate