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700029

Sigma-Aldrich

SIMes-leucinol

97%

Synonym(s):

1-(S)-Leucinol-3-(2,4,6-trimethylphenyl)-3H-imidazolium hexafluorophosphate

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About This Item

Empirical Formula (Hill Notation):
C18H27F6N2OP
Molecular Weight:
432.38
UNSPSC Code:
12352101
PubChem Substance ID:
329762174

Assay

97%

form

powder

reaction suitability

reaction type: click chemistry
reagent type: catalyst

mp

168-170 °C

storage temp.

2-8°C

SMILES string

F[P-](F)(F)(F)(F)F.CC(C)C[C@@H](CO)[N+]1=CN(CC1)c2c(C)cc(C)cc2C

InChI

1S/C18H29N2O.F6P/c1-13(2)8-17(11-21)19-6-7-20(12-19)18-15(4)9-14(3)10-16(18)5;1-7(2,3,4,5)6/h9-10,12-13,17,21H,6-8,11H2,1-5H3;/q+1;-1/t17-;/m0./s1

InChI key

NTQWYGMQOMHOQG-LMOVPXPDSA-N

Application

Chiral NHC used with copper for conjugate addition of Grignards to enones

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Precautionary Statements

P280 - P305 + P351 + P338 - P310

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8B - Non-combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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David Martin et al.
Journal of the American Chemical Society, 128(26), 8416-8417 (2006-06-29)
The copper-catalyzed asymmetric conjugate addition of Grignard reagents to trisubstituted cyclic enones affords enantioenriched all-carbon quaternary centers with up to 96% ee. The chiral ligand is a diaminocarbene, directly generated in situ. The combination of Grignard reagent and diaminocarbene is

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