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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.

Related Content

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.

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