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(1S,1″S,2S,2″S,5R,5″R)-5,5″-Dimethyl-2,2″-bis(1-methylethyl)-dispiro[cyclohexane-1,3′(2′H)-imidazo[5,1-b:4,3-b′]bisoxazol[4]ium-7′(8′H),1″-cyclohexane]1,1,1-trifluoromethanesulfonate

  1. Thomas Dröge1,
  2. Frank Glorius2

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01623

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Dröge, T. and Glorius, F. 2013. (1S,1″S,2S,2″S,5R,5″R)-5,5″-Dimethyl-2,2″-bis(1-methylethyl)-dispiro[cyclohexane-1,3′(2′H)-imidazo[5,1-b:4,3-b′]bisoxazol[4]ium-7′(8′H),1″-cyclohexane]1,1,1-trifluoromethanesulfonate. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. 1

    University of Michigan, Ann Arbor, MI, USA

  2. 2

    University of Münster, Münster, Germany

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

(stable precursor to the free sterically demanding N heterocyclic carbene (NHC),1 which is used as a ligand in asymmetric transition metal catalyzed transformations)

Alternate Name: IBiox[(−)-menthyl]·HOTf.

Physical Data: ρcalc = 1.277 kg m−3.

Solubility: soluble in CH2Cl2, methanol, and DMSO; slightly soluble in THF; insoluble in benzene and diethyl ether.

Form Supplied in: colorless crystals, not widely available.

Analysis of Reagent Purity:1H and 13C NMR spectroscopy, elemental analysis, optical rotation.

Preparative Method: IBiox[(−)-menthyl]·HOTf is prepared from enantiopure (−)-menthone.2 In a first sequence, (−)-menthone is converted through a diastereoselective Bucherer–Bergs reaction into the corresponding hydantoin followed by hydrolysis under forcing acidic conditions to the α-amino acid.3, 4 Reduction of the crude amino acid with sodium borohydride/I2 in THF yields the optically active amino alcohol.5 In a second sequence, heating of the amino alcohol with diethyl oxalate in toluene generates the symmetric bisamide. Chlorination with thionyl chloride and cyclization under strongly basic conditions results in the 2,2′-bisoxazoline.6 Finally, reacting the bisoxazoline with a pretreated mixture of silver(I) trifluoromethanesulfonate and pivaloyloxymethyl chloride results in the formation of the desired bisoxazol-imidazolium salt.7

Purification: flash column chromatography on silica gel with a solvent mixture gradient of CH2Cl2–methanol (99:1–91:9) followed by recrystallization from CH2Cl2 by the addition of diethyl ether.

Handling, Storage, and Precautions: air and moisture stable (potentially hygroscopic).

Featured Compounds

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  1. 1 - 52
Compound Information
Molecular Weight:550.674
Molecular Formula:C26H42F3N2O5S
InChIKey:OVMNFZWKDCTGOH-JSWGGJIYSA-M
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Compound Information
Molecular Weight:400.5973
Molecular Formula:C25H40N2O2
InChIKey:NNUBWWDZEWEKPZ-OGGCUATRSA-N
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Compound Information
Molecular Weight:96.1034
Molecular Formula:C4H9NaO
InChIKey:MFRIHAYPQRLWNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:80.155
Molecular Formula:C4H8O
InChIKey:Not Available
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Compound Information
Molecular Weight:588.369
Molecular Formula:C25H40AgBrN2O2
InChIKey:LJOFWRLGIHCGCX-RTNQAOHWSA-M
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Compound Information
Molecular Weight:231.7358
Molecular Formula:Ag2O
InChIKey:NDVLTYZPCACLMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.894
Molecular Formula:BrNa
InChIKey:JHJLBTNAGRQEKS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:388.757
Molecular Formula:C4Cl2O4Rh2
InChIKey:FGKDXBICTVUSPK-UHFFFAOYSA-L
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Compound Information
Molecular Weight:594.976
Molecular Formula:C27H40ClN2O4Rh
InChIKey:QAHPXQQZTZFQNY-PBMOQUBVSA-M
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Compound Information
Molecular Weight:1133.932
Molecular Formula:C52H80Cl2N4O6Rh2
InChIKey:CVGNLERKMYWCSY-WCAWNUJCSA-L
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Compound Information
Molecular Weight:365.89
Molecular Formula:C6H10Cl2Pd2
InChIKey:OTBRMLNJALKXGN-UHFFFAOYSA-L
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Compound Information
Molecular Weight:583.54
Molecular Formula:C28H45ClN2O2Pd
InChIKey:CUEMOLARYKHKMG-DAEXQNHMSA-M
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1155.85
Molecular Formula:C50H80Cl4N4O4Pd2
InChIKey:CISMECCYAMKJPI-WCAWNUJCSA-J
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Compound Information
Molecular Weight:224.51
Molecular Formula:C4H6O4Pd
InChIKey:YJVFFLUZDVXJQI-UHFFFAOYSA-L
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Compound Information
Molecular Weight:42.394
Molecular Formula:ClLi
InChIKey:KWGKDLIKAYFUFQ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:575
Molecular Formula:C34H28O2Pd
InChIKey:UKSZBOKPHAQOMP-SVLSSHOZSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:XTHFKEDIFFGKHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:160.2124
Molecular Formula:C11H12O
InChIKey:GANIBVZSZGNMNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.008
Molecular Formula:C6H5Br
InChIKey:QARVLSVVCXYDNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3083
Molecular Formula:C17H16O
InChIKey:FHONLNCEDWDJSX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:187.034
Molecular Formula:C7H7BrO
InChIKey:PLDWAJLZAAHOGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:266.3343
Molecular Formula:C18H18O2
InChIKey:VZAXUDUNDHPCCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:229.071
Molecular Formula:C9H9BrO2
InChIKey:VYPYKCPWNPPBBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:308.371
Molecular Formula:C20H20O3
InChIKey:YOBIQBPXEXJPHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:1728.908
Molecular Formula:C79H120Cl3N6O10Rh3
InChIKey:ARBKNPMCGIOKBB-OOZDKWICSA-K
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Compound Information
Molecular Weight:325.8198
Molecular Formula:CCs2O3
InChIKey:FJDQFPXHSGXQBY-UHFFFAOYSA-L
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:121.93
Molecular Formula:C6H7BO2
InChIKey:HXITXNWTGFUOAU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:157.363
Molecular Formula:C5H5BClNO2
InChIKey:WPAPNCXMYWRTTL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:219.442
Molecular Formula:C5H3BClF3KN
InChIKey:TVBXAWSXJKYPGJ-UHFFFAOYSA-N
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