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New chiral N,P-oxazolines, and their Ir complexes in asymmetric hydrogenation of an imine

TitleNew chiral N,P-oxazolines, and their Ir complexes in asymmetric hydrogenation of an imine
Publication TypeJournal Article
Year of Publication2004
AuthorsEzhova, MB, Patrick, BO, James, BR, Waller, FJ, Ford, ME
JournalJournal of Molecular Catalysis a-Chemical
Volume224
Pagination71-79
Date PublishedDec
Type of ArticleArticle
ISBN Number1381-1169
Keywords2-OXAZOLINES, ALLYLIC, ASYMMETRIC HYDROGENATION, CATALYZED ENANTIOSELECTIVE HYDROGENATION, imines, Ir complexes, JM-PHOS LIGANDS, KETONES, LIGANDS, oxazolines, PHOSPHINITE-OXAZOLINE, PHOSPHINOOXAZOLINES, PHOSPHORUS, SEMICORRINS, SUBSTITUTION, TRANSITION-METAL-COMPLEXES, X-ray analysis
Abstract

{(+) (1S.2S)-2-Amino-1-phenyl-13-propanediol reacts with ortho-esters to form 4-hydroxymethyl-5-phenyl-1,3-oxazolines. Subsequent reaction of their toluenesulfonyl derivatives with diphenylphosphinolithium yields the N,P-ligands, (4S,5S)-2-R-4-diphenylphosphinomethyl-5-phenyl- 1.3-oxazoline (R = Me, Et, Ph). X-ray analyses of (4S,5S)-2-methyl-4-toluenesulfonylmethyl-5-phenyl- 1,3-oxazoline and (4S,5S)-2,5-diphenyl-4-diphenylphosphinomethyl-1,3-oxazoline reveal retention of absolute configuration throughout the synthesis. The [Ir(COD)(N,P-oxazoline)]PF6 systems in CH2Cl2 effect catalytic hydrogenation of N-(1 -phenylethylidene)benzylamine
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