Enantioselective Palladium-Catalyzed Diamination of Alkenes Using N‑Fluorobenzenesulfonimide

An enantioselective Pd-catalyzed vicinal diamination of unactivated alkenes using N-fluorobenzenesulfonimide as both an oxidant and a source of nitrogen is reported. The use of Ph-pybox and Ph-quinox ligands afforded differentially protected vicinal diamines in good yields with high enantioselectivi...

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Published inJournal of the American Chemical Society Vol. 135; no. 24; pp. 8854 - 8856
Main Authors Ingalls, Erica L, Sibbald, Paul A, Kaminsky, Werner, Michael, Forrest E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.06.2013
Amer Chemical Soc
Subjects
alkenes
catalysts
Chemistry
Chemistry, Multidisciplinary
diamines
enantiomers
ligands
nitrogen
oxidants
palladium
Physical Sciences
Science & Technology
X-ray diffraction
OLEFINS
ASYMMETRIC DIAMINATION
CONJUGATED DIENES
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ISSN0002-7863
1520-5126
1520-5126
DOI10.1021/ja4043406

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Summary:An enantioselective Pd-catalyzed vicinal diamination of unactivated alkenes using N-fluorobenzenesulfonimide as both an oxidant and a source of nitrogen is reported. The use of Ph-pybox and Ph-quinox ligands afforded differentially protected vicinal diamines in good yields with high enantioselectivities. Mechanistic experiments revealed that the high enantioselectivity arises from selective formation of only one of four possible diastereomeric aminopalladation products of the chiral Pd complex. The aminopalladation complex was characterized by X-ray crystallography.
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja4043406