Cerium ammonium nitrate (CAN) for mild and efficient reagent to remove hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines

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• 作者：Hiromichi Fujioka ; Hideki Hirose ; Yusuke Ohba ; Kenichi Murai ; Kenji Nakahara ; Yasuyuki Kita
• 关键词：CAN ; Removal of hydroxyethyl unit ; 2-Hydroxyethyl ether ; 2-Hydroxyethyl amine
• 刊名：Tetrahedron
• 出版年：2007
• 出版时间：15 January 2007
• 年：2007
• 卷：63
• 期：3
• 页码：625-637
• 全文大小：649 K

文摘

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 C₂-symmetric diols, chiral 2,3-butanediol and chiral hydrobenzoin, was very useful for asymmetric syntheses using C₂-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.