Preparation of acetals from aldehydes and alcohols under basic conditions. Issue 17 (22nd February 2018)

• Record Type: Journal Article
• Authors: Grabowski, Jakub; Granda, Jarosław M.; Jurczak, Janusz
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 17(2018)
• Page Start: 3114
• Page End: 3120
• Publication Date: 2018-02-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00017d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A new method for acetalization of aldehydes under basic conditions, which enables protection in the presence of acid-sensitive groups, has been described. Abstract : A new, simple protocol for the synthesis of acetals under basic conditions from non-enolizable aldehydes and alcohols has been reported. Such reactivity is facilitated by a sodium alkoxide along with a corresponding trifluoroacetate ester, utilizing formation of sodium trifluoroacetate as a driving force for acetal formation. The usefulness of this protocol is demonstrated by its orthogonality with various acid-sensitive protecting groups and by good compatibility with functional groups, delivering synthetically useful acetals complementarily to the synthesis under acidic conditions from aldehydes and alcohols.