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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)

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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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
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
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)

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