Isomer-sensitive deboronation in reductive aminations of aryl boronic acids. Issue 42 (14th October 2015)

• Record Type: Journal Article
• Authors: Jones, Brad H.; Wheeler, David R.; Wheeler, Jill S.; Miller, Lance L.; Alam, Todd M.; Spoerke, Erik D.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 42(2015)
• Page Start: 5731
• Page End: 5734
• Publication Date: 2015-10-14
• Subjects: Boronic acid -- Reductive amination -- Peptide modification -- Deboronation -- Formylphenylboronic acid; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.09.006
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: Deboronation is observed during the reductive amination of formylphenylboronic acid (FPBA) to the amine termini and side chains of peptides. This deboronation is sensitive to the isomerism of the boronic acid (BA), with ortho -FPBA yielding complete deboronation in the preparation of an N-terminally-modified dipeptide. The observed behavior is also clearly mediated by the chemical identity of the amine substrate. These results reveal a previously undocumented subtlety of BA functionalization and highlight the importance of thorough spectroscopic characterization in the preparation of peptide and small molecule BAs.