Iridium-N,P-Ligand-Catalyzed Enantioselective Hdyrogenation of Diphenylvinylphosphine Oxides and Vinylphosphonates

Diphenylvinylphosphine oxides and di- and trisubstituted vinylphosphonates have been employed as substrates in iridium-catalyzed asymmetric hydrogenations. Complete conversions and excellent enantioselectivities (up to and above 99% ee) were observed for a range of substates with both aromatic and a...

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Published inJournal of the American Chemical Society Vol. 131; no. 23; pp. 8285 - 8289
Main Authors Cheruku, Pradeep, Paptchikhine, Alexander, Church, Tamara L., Andersson, Pher G.
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 17.06.2009
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CATALYZED ASYMMETRIC HYDROGENATION
SUBSTITUTED FOSMIDOMYCIN ANALOGS
PHOSPHORUS LIGANDS
ALPHA,BETA-UNSATURATED ALDEHYDES
ANTIMALARIAL ACTIVITY
TRISUBSTITUTED OLEFINS
OXAZOLINE LIGANDS
IRIDIUM CATALYSTS
CHIRAL DIPHOSPHINE
AQUEOUS-SOLUTION
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Summary:Diphenylvinylphosphine oxides and di- and trisubstituted vinylphosphonates have been employed as substrates in iridium-catalyzed asymmetric hydrogenations. Complete conversions and excellent enantioselectivities (up to and above 99% ee) were observed for a range of substates with both aromatic and aliphatic groups at the prochiral carbon. We have also hydrogenated electron-deficient carboxyethylvinylphosphonates with excellent stereoselectivity (up to and above 99% ee). The hydrogenated products of both classes of substrates are synthetically useful intermediates.
ISSN:0002-7863
DOI:10.1021/ja901437t