Zinc-Catalyzed Esterification of N-beta-Hydroxyethylamides: Removal of Directing Groups under Mild Conditions

Nishii, Yuji; Hirai, Takahiro; Fernandez, Sarah; Knochel, Paul and Mashima, Kazushi (2017): Zinc-Catalyzed Esterification of N-beta-Hydroxyethylamides: Removal of Directing Groups under Mild Conditions. In: European Journal of Organic Chemistry, No. 34: pp. 5010-5014

Abstract

Amide transformations involving C-N bond cleavage are recognized as difficult reactions owing to the inert nature of amides resulting from resonance. Accordingly, a strong inductive effect and geometrical distortion reasonably decrease the resonance stabilization to attenuate the C-N linkage. Although the conversion of such activated amides has been studied intensively, reaction systems for unactivated amides are underdeveloped. We herein report that a zinc(II) trifluoromethanesulfonate [Zn(OTf)(2)] catalyst achieves the esterification of a wide range of unactivated tertiary amides with the assistance of intramolecular acyl rearrangement. The reaction was applied to the one-pot removal of various amide-based directing groups under mild reaction conditions to afford the corresponding esters in high yields.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1434-193X
• Language: English