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688495

Sigma-Aldrich

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

97%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C25H26NOP
Número de CAS:
148461-16-9
Peso molecular:
387.45
MDL number:
MFCD09998277
UNSPSC Code:
12352005
PubChem Substance ID:
329761168
NACRES:
NA.22

assay

97%

form

solid

optical activity

[α]22/D -57.0°, c = 1 in chloroform

mp

111-116 °C

functional group

ether
phosphine

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
MKBQ4066V
MKBK7581V
MKBD1693
MKBC3713
08808KH

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PHOX
Aldrich Chemfiles, 8(2) null

Artículos

PHOX

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

PHOX

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

PHOX

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

PHOX

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

Contenido relacionado

Pfaltz Group – Professor Product Portal

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.

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

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