Synthesis of N-Acyl-N,O-Acetals from N-Aryl Amides and Acetals in the Presence of TMSOTf

Authors

C. Wade Downey, University of RichmondFollow
Alan S. Fleisher
James T. Rague
Chelsea L. Safran
Megan E. Venable
Robert D. Pike

DOI

doi:10.1016/j.tetlet.2011.07.023

Abstract

Secondary amides undergo in situ silyl imidate formation mediated by TMSOTf and an amine base, followed by addition to acetal acceptors to provide N-acyl-N,O-acetals in good yields. An analogous, high-yielding reaction is observed with 2-mercaptothiazoline as the silyl imidate precursor. Competing reduction of the acetal to the corresponding methyl ether via transfer hydrogenation can be circumvented by the replacement of i-Pr₂NEt with 2,6-lutidine under otherwise identical reaction conditions.

Document Type

Post-print Article

Publication Date

9-12-2011

Publisher Statement

Copyright © 2011, Elsevier. The definitive version is available at: http://www.journals.elsevier.com/tetrahedron-letters.

DOI: 10.1016/j.tetlet.2011.07.023

Full Citation:

Downey, C. Wade, Alan S. Fleisher, James T. Rague, Chelsea L. Safran, Megan E. Venable, and Robert D. Pike. "Synthesis of N-Acyl-N,O-Acetals from N-Aryl Amides and Acetals in the Presence of TMSOTf." Tetrahedron Letters 52, no. 37 (September 12, 2011): 4756-759. doi:10.1016/j.tetlet.2011.07.023.

Recommended Citation

Downey, C. Wade; Fleisher, Alan S.; Rague, James T.; Safran, Chelsea L.; Venable, Megan E.; and Pike, Robert D., "Synthesis of N-Acyl-N,O-Acetals from N-Aryl Amides and Acetals in the Presence of TMSOTf" (2011). Chemistry Faculty Publications. 12.
https://scholarship.richmond.edu/chemistry-faculty-publications/12