SYNTHESIS OF CHIRAL (PHOSPHINOARYL)OXAZOLINES, A VERSATILE CLASS OF LIGANDS FOR ASYMMETRIC CATALYSIS

Enantiomerically pure 2-[2-(diphenylphosphino)aryl]oxazolines are readily prepared from 2-bromobenzonitrile by transmetalation with BuLi, subsequent reaction with chlorodiphenylphosphine and conversion of the resulting phosphinoaryl nitrile to the oxazoline by treatment with a chiral amino alcohol i...

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Bibliographic Details
Published inRECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY Vol. 114; no. 4-5; pp. 206 - 210
Main Authors KOCH, G, LLOYDJONES, GC, LOISELEUR, O, PFALTZ, A, PRETOT, R, SCHAFFNER, S, SCHNIDER, P, VONMATT, P
Format Journal Article
LanguageEnglish
Published AMSTERDAM Elsevier 1995
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ORTHO LITHIATION
REDUCTION
CHIRAL OXAZOLINES
AMINO-ACIDS
AMINO ALCOHOLS
CHIRAL P,N-LIGANDS
ALLYLIC SUBSTITUTION
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Summary:Enantiomerically pure 2-[2-(diphenylphosphino)aryl]oxazolines are readily prepared from 2-bromobenzonitrile by transmetalation with BuLi, subsequent reaction with chlorodiphenylphosphine and conversion of the resulting phosphinoaryl nitrile to the oxazoline by treatment with a chiral amino alcohol in the presence of ZnCl2. An alternative synthesis is based on the orthometalation of 2-aryloxazolines followed by reaction with chlorodiphenylphosphine.
ISSN:0165-0513
DOI:10.1002/recl.19951140413