Cerium ammonium nitrate (CAN) for mild and efficient reagent to remove hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines
作者:Hiromichi Fujioka、Hideki Hirose、Yusuke Ohba、Kenichi Murai、Kenji Nakahara、Yasuyuki Kita
DOI:10.1016/j.tet.2006.11.004
日期:2007.1
Cerium ammonium nitrate (CAN) removed hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines to produce alcohols and amines in good yields. Especially, removal of the 2-hydroxyethyl ethers from C-2-symmetric diols, chiral 2,3-butanediol and chiral hydrobenzoin, was very useful for asymmetric syntheses using C-2-symmetric diols. The reactions using dual abilities of CAN, i.e., the ability for removal of the 2-hydroxyethyl unit and the ability for acetal hydrolysis by a single electron transfer, were also achieved Successfully. The reaction conditions were very mild and efficient, and many functional groups, which can be affected under normal conditions, were unaffected during the reaction. (c) 2006 Published by Elsevier Ltd.