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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:
148461-16-9
Molecular Weight:
387.45
MDL number:
MFCD09998277
UNSPSC Code:
12352005
PubChem Substance ID:
329761168
NACRES:
NA.22

Quality Level

100

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBQ4066V
MKBK7581V
MKBD1693
MKBC3713
08808KH

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PHOX
Aldrich Chemfiles, 8(2) null

Articles

PHOX

Of the thousands of chiral ligands used in asymmetric synthesis a relatively large number exhibit C2-symmetry. More recently, non-symmetrical modular P,N-ligands have been introduced independently by Pfaltz, Helmchen, and Williams and applied successfully in various metal-catalyzed reactions.

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