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

G  KOCH; G C  LLOYDJONES; O  LOISELEUR; A  PFALTZ; R  PRETOT; S  SCHAFFNER; P  SCHNIDER; P  VONMATT; Guy C Lloyd-Jones

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

G KOCH, G C LLOYDJONES, O LOISELEUR, A PFALTZ, R PRETOT, S SCHAFFNER, P SCHNIDER, P VONMATT, Guy C Lloyd-Jones

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

78 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	206-210
Number of pages	5
Journal	Recueil des Travaux Chimiques des Pays-Bas (Journal of the Royal Netherlands Chemical Society)
Volume	114
Issue number	4-5
Publication status	Published - 1995

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@article{208bef9135f042789c914e19a7628956,

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

abstract = "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.",

author = "G KOCH and LLOYDJONES, {G C} and O LOISELEUR and A PFALTZ and R PRETOT and S SCHAFFNER and P SCHNIDER and P VONMATT and Lloyd-Jones, {Guy C}",

year = "1995",

language = "English",

volume = "114",

pages = "206--210",

journal = "Recueil des Travaux Chimiques des Pays-Bas (Journal of the Royal Netherlands Chemical Society)",

issn = "0165-0513",

publisher = "Royal Netherlands Chemical Society",

number = "4-5",

}

SYNTHESIS OF CHIRAL (PHOSPHINOARYL)OXAZOLINES, A VERSATILE CLASS OF LIGANDS FOR ASYMMETRIC CATALYSIS. / KOCH, G ; LLOYDJONES, G C ; LOISELEUR, O et al.
In: Recueil des Travaux Chimiques des Pays-Bas (Journal of the Royal Netherlands Chemical Society), Vol. 114, No. 4-5, 1995, p. 206-210.

Research output: Contribution to journal › Article (Academic Journal) › peer-review

TY - JOUR

T1 - SYNTHESIS OF CHIRAL (PHOSPHINOARYL)OXAZOLINES, A VERSATILE CLASS OF LIGANDS FOR ASYMMETRIC CATALYSIS

AU - KOCH, G

AU - LLOYDJONES, G C

AU - LOISELEUR, O

AU - PFALTZ, A

AU - PRETOT, R

AU - SCHAFFNER, S

AU - SCHNIDER, P

AU - VONMATT, P

AU - Lloyd-Jones, Guy C

PY - 1995

Y1 - 1995

N2 - 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.

AB - 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.

M3 - Article (Academic Journal)

SN - 0165-0513

VL - 114

SP - 206

EP - 210

JO - Recueil des Travaux Chimiques des Pays-Bas (Journal of the Royal Netherlands Chemical Society)

JF - Recueil des Travaux Chimiques des Pays-Bas (Journal of the Royal Netherlands Chemical Society)

IS - 4-5

ER -

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

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