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699918

Sigma-Aldrich

(R)-N-[(1R,2R)-2-(3-(3,5-Bis(trifluoromethyl)phenyl)ureido)cyclohexyl]-tert-butyl-sulfinamide

96%

Synonym(s):

[S(R)]-N-[(1R,2R)-2-[[[[3,5-Bis(trifluoromethyl)phenyl]amino]carbonyl]amino]cyclohexyl]-2-methyl-2-propanesulfinamide

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About This Item

Empirical Formula (Hill Notation):
C19H25F6N3O2S
CAS Number:
934762-68-2
Molecular Weight:
473.48
MDL number:
MFCD11656068
UNSPSC Code:
12352002
PubChem Substance ID:
329762164
NACRES:
NA.22

Assay

96%

form

solid

mp

173-181 °C

SMILES string

CC(C)(C)S(=O)N[C@@H]1CCCC[C@H]1NC(=O)Nc2cc(cc(c2)C(F)(F)F)C(F)(F)F

InChI

1S/C19H25F6N3O2S/c1-17(2,3)31(30)28-15-7-5-4-6-14(15)27-16(29)26-13-9-11(18(20,21)22)8-12(10-13)19(23,24)25/h8-10,14-15,28H,4-7H2,1-3H3,(H2,26,27,29)/t14-,15-,31-/m1/s1

InChI key

WMIJNZVQFOPOBW-ZHANGXNJSA-N

Application

(R)-N-[(1R,2R)-2-(3-(3,5-Bis(trifluoromethyl)phenyl)ureido)cyclohexyl]-tert-butyl-sulfinamide is a sulfinamide-urea based chiral catalyst that can be used to synthesize:
  • Enantioselective homoallylic amines by asymmetric allylation of acylhydrazones with allylindium reagents.
  • Tetrahydroquinolines via an asymmetric Povarov reaction.
  • 2-aryl-substituted cycloalkanones by enantioselective protonation of corresponding trimethylsilyl enol ethers.

Hazard Statements

H413

Hazard Classifications

Aquatic Chronic 4

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

Certificates of Analysis (COA)

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Indium-mediated asymmetric allylation of acylhydrazones using a chiral urea catalyst.
Kian L Tan et al.
Angewandte Chemie (International ed. in English), 46(8), 1315-1317 (2007-01-11)
Elizabeth M Beck et al.
Organic letters, 13(16), 4260-4263 (2011-07-27)
The application of chiral sulfinamides and achiral sulfonic acids as a cocatalyst system for enantioselective protonation reactions is described. Structurally simple, easily accessible sulfinamides were found to induce moderate-to-high ee's in the formation of 2-aryl-substituted cycloalkanones from the corresponding trimethylsilyl
Baudouin Gerard et al.
ACS combinatorial science, 14(11), 621-630 (2012-10-24)
A 2328-membered library of 2,3,4-trisubstituted tetrahydroquinolines was produced using a combination of solution- and solid-phase synthesis techniques. A tetrahydroquinoline (THQ) scaffold was prepared via an asymmetric Povarov reaction using cooperative catalysis to generate three contiguous stereogenic centers. A matrix of

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