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795682

Sigma-Aldrich

(4R,4′R,5S,5′S)-2,2′-(1-Methylethylidene

95%

Synonym(s):

2,2-Bis[2-(4R,5S-diphenyl-1,3-oxazolinyl)]propane

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About This Item

Empirical Formula (Hill Notation):
C33H30N2O2
CAS Number:
157904-67-1
Molecular Weight:
486.60
MDL number:
MFCD24849939
UNSPSC Code:
12352005
PubChem Substance ID:
329768502
NACRES:
NA.22

Quality Level

100

assay

95%

form

solid

mp

164-169 °C

SMILES string

CC(C1=N[C@H](C2=CC=CC=C2)[C@H](C3=CC=CC=C3)O1)(C)C4=N[C@H](C5=CC=CC=C5)[C@H](C6=CC=CC=C6)O4

InChI

1S/C33H30N2O2/c1-33(2,31-34-27(23-15-7-3-8-16-23)29(36-31)25-19-11-5-12-20-25)32-35-28(24-17-9-4-10-18-24)30(37-32)26-21-13-6-14-22-26/h3-22,27-30H,1-2H3/t27-,28-,29+,30+/m1/s1

InChI key

ZWWGNCSTEMMQOQ-XAZDILKDSA-N

Application

(4R,4′R,5S,5′S)-2,2′-(1-Methylethylidene) or (4S,5R)-Bis-Phbox) can be used as a ligand:
  • To prepare selective exo-catalysts for enantioselective 1,3-dipolar cycloaddition reactions.
  • In the asymmetric aminooxygenation of alkenes in the presence of tetramethylaminopyridyl radical (TEMPO) as an oxidant and copper(II) triflate as a catalyst.
  • In asymmetric aminofluorination of olefins using an iron catalyst.

This chiral Box ligand was most recently shown to mediate an asymmetric aminofluorination of olefins utlizing Xtalfuor-E (719439) and TREAT-HF (344648). The resulting cyclic carbamates can be readily converted into their concomitant beta-fluoro amino acids.

Other Notes

Iron(II)-Catalyzed Intramolecular Olefin Aminofluorination

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes
Fuller PH, et al.
Journal of the American Chemical Society, 130(52), 17638-17639 (2008)
In Search of exo-Selective Catalysts for Enantioselective 1, 3-Dipolar Cycloaddition between Acryloyloxazolidinone and Diphenylnitrone
Desimoni G, et al.
European Journal of Organic Chemistry, 2005(6), 1020-1027 (2005)
Iron (II)-catalyzed intramolecular olefin aminofluorination
Lu Deng-Fu, et al.
Organic Letters, 16(11), 2912-2915 (2014)

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