Effect of Substituents and Stability of Transient Aluminum-Aminals in the Presence of Nucleophiles

Francis J Barrios; Brannon C Springer; Robert A Hazlitt; David A Colby

doi:10.1055/s-0034-1379635

Effect of Substituents and Stability of Transient Aluminum-Aminals in the Presence of Nucleophiles

Synthesis (Stuttg). 2015 Jan;47(2):175-180. doi: 10.1055/s-0034-1379635. Epub 2014 Dec 5.

Authors

Francis J Barrios¹, Brannon C Springer², Robert A Hazlitt³, David A Colby³

Affiliations

¹ Department of Chemistry and Physics, Bellarmine University, 2001 Newburg Rd., Louisville, Kentucky 40205.
² Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907.
³ Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907; Department of BioMolecular Sciences, University of Mississippi, 317 Faser Hall, P. O. Box 1848, University, Mississippi 38677.

Abstract

Disubstituted hydroxylamines were synthesized and used to form aluminum-amide complexes. These reagents masked carbonyl groups in situ from nucleophilic addition. The stability and utility of the aluminum-aminals are presented in the context of selectively controlling nucleophilic addition on substrates with multiple carbonyl groups.

Keywords: aluminum; amides; amines; carbonyl complexes; nucleophilic addition.

Abstract

Grants and funding