ACID-CATALYZED TRANSACETALIZATION FROM GLYCOL TO PINACOL ACETALS

作者:Seeleib Yvonne; Nemecek Gregor; Pfaff Dominik; Sueveges Bastian D; Podlech Joachim*
来源:Synthetic Communications, 2014, 44(20): 2966-2973.
DOI:10.1080/00397911.2014.912330

摘要

A one-pot transacetalization of glycol acetals, frequently used as protecting groups of the aldehyde function, into the more stable pinacol acetals is given. A clean transformation of aromatic and aliphatic substrates is possible with trifluoroacetic acid within 30 min at 0 degrees C. Glycol acetals derived from ketones (ketals) cannot be converted with this protocol. Deprotection of the pinacol acetals is possible with trifluoromethanesulfonic acid in the presence of water.

  • 出版日期2014