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(1S)-3-(1,10-Phenanthrolin-2-yl)-2'-phenyl-[1,1'-binaphthalen]-2-ol
(CAS Number:1621903-81-8 Product Number:P2599)

Structure

(1S)-3-(1,10-Phenanthrolin-2-yl)-2'-phenyl-[1,1'-binaphthalen]-2-ol
Synonym (S)-BinThro

General Information

Product Number P2599

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Purity/Analysis Method >97.0%(HPLC)
Storage Temperature
M.F. / M.W. C38H24N2O=524.62
CAS Number 1621903-81-8
Related CAS Number
MDL Number
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Specification

Elemental analysis(Nitrogen) 5.10 to 5.60 %
Purity(HPLC) min. 97.0 area%
Specific rotation(value) 19.0 to 21.0 deg

References

Reaxys-RN 28138987

Transport Information

HS Number 2933.99.8290

Application

A Novel Phenanthroline Chiral Ligand for Versatile Asymmetric Metal Catalysis, (S)-BinThro

(S)-BinThro is a new class of phenanthroline ligand bearing an axially chiral binaphthyl backbone, developed by Naganawa and Nishiyama et al. (S)-BinThro provides the N,N,O-tridentate coordination of the phen moiety with a phenolic hydroxyl group. As phen possesses greater coordination ability with various ions, (S)-BinThro would apply to a broad range of asymmetric metal catalysts (Cu1-3), Rh1,4), Ni1,5), Zn1,6)) and several enantioselective reactions.

Typical Procedure (Asymmetric Davis oxidation1,2)): To a mixture of (S)-BinThro (2.9 mg, 5.5 μmol) and Cu(OAc)2·H2O (1.0 mg, 5.0 μmol) in a Schlenk tube under Ar atmosphere, dry diethyl ether (1 mL) is added at 25 °C. After stirring for 1 h at 25 °C, the oxindole (30.9 mg, 0.1 mmol) is added portion-wise to the mixture. After stirring another 5 min, Davis’ oxaziridine (33.0 mg, 0.12 mmol) is added portion-wise to the mixture and stirred for 24 h at the same temperature. The catalyst is removed by passing through short column chromatography on silica gel (eluting chloroform) and the solvent is evaporated. The residue is purified by column chromatography on silica gel (eluting hexane/EtOAc) to give the desired oxidation product (>99% yield, 93% ee).

References

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