Synthesis 2015; 47(02): 175-180
DOI: 10.1055/s-0034-1379635
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© Georg Thieme Verlag Stuttgart · New York

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

Francis J. Barrios
a  Department of Chemistry and Physics, Bellarmine University, 2001 Newburg Rd., Louisville, KY 40205, USA
,
Brannon C. Springer
b  Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA
,
Robert A. Hazlitt
b  Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA
c  Department of BioMolecular Sciences, University of Mississippi, 317 Faser Hall, P.O. Box 1848, University, MS 38677, USA   eMail: dacolby@olemiss.edu
,
David A. Colby*
b  Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USA
c  Department of BioMolecular Sciences, University of Mississippi, 317 Faser Hall, P.O. Box 1848, University, MS 38677, USA   eMail: dacolby@olemiss.edu
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Publikationsverlauf

Received: 15. Oktober 2014

Accepted after revision: 17. November 2014

Publikationsdatum:
05. Dezember 2014 (online)


Abstract

Disubstituted hydroxylamines are synthesized and used to form aluminum–amide complexes. These reagents mask carbonyl groups in situ via 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.

 
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