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Sigma-Aldrich

(S)-4-tert-Butyl-2-[2-(diphenylphosphino)phenyl]-2-oxazoline

97%

Synonym(s):

(4S)-tert-Butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydrooxazole

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About This Item

Empirical Formula (Hill Notation):
C25H26NOP
CAS Number:
Molecular Weight:
387.45
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

solid

optical activity

[α]22/D -57.0°, c = 1 in chloroform

mp

111-116 °C

storage temp.

−20°C

SMILES string

CC(C)(C)[C@@H]1N=C(C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)OC1

InChI

1S/C25H26NOP/c1-25(2,3)23-18-27-24(26-23)21-16-10-11-17-22(21)28(19-12-6-4-7-13-19)20-14-8-5-9-15-20/h4-17,23H,18H2,1-3H3/t23-/m1/s1

InChI key

DMOLTNKQLUAXPI-HSZRJFAPSA-N

Related Categories

General description

The product is a phosphinooxazoline (PHOX) ligand introduced by Pfaltz and coworkers. These non-symmetrical modular P,N-ligands are particularly useful in cases where double bond migration leads to undesired products or mixtures of isomers.

Application

(S)-4-tert-Butyl-2-[2-(diphenylphosphino)phenyl]-2-oxazoline can be used as a ligand for enantioselective Heck reaction without any C=C double bond migration byproduct. It can also be used in a rhodium(I)-catalyzed enantioselective desymmetrization reaction of meso-3,5-dimethyl glutaric anhydride, to form substituted syn-deoxypolypropionate fragments in a single transformation.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

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PHOX
Aldrich Chemfiles, 8(2) null

Articles

Modular P,N-ligands in asymmetric synthesis introduced by Pfaltz, Helmchen, and Williams exhibit success in metal-catalyzed reactions.

Related Content

Andreas Pfaltz has a longstanding interest in the design of chiral ligands for asymmetric catalysis. The semicorrins developed in his group served as the prototype for an important family of nitrogen ligands, the bisoxazolines, which have found widespread use in catalytic asymmetric synthesis.

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