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Product Information

Product Name
1-3,5-Bis(trifluoromethyl)phenyl-3-(1R,2R)-2-(dimethylamino)cyclohexylthiourea, 98%, (99% ee)
Brand Name
US-Strem
Product Number
07-6331
CAS
620960-26-1
Certificate of Analysis (COA)​
COA not found

General Information

PubChem CID
11486766
IUPAC Name
1-3,5-bis(trifluoromethyl)phenyl-3-(1R,2R)-2-(dimethylamino)cyclohexylthiourea
InChI Key
NQRCAVZHOLYEBJ-ZIAGYGMSSA-N
SMILES
CN(C)C@@H1CCCCC@H1NC(=S)NC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F

Application

Technical Notes:
1. Michael Addition- Michael reaction of malonates to afforded Michael adducts with high yields and enantioselectivities (up to 95%, up to 93% ee).
2.Synthesized a new class of bifunctional catalysts bearing a thiourea moiety and an amino group on a chiralscaffold.
3.A thiourea-catalyzed asymmetric Michael addition of activated methylene compounds to a,ß-unsaturated imides derived from 2-pyrrolidinone and 2-methoxybenzamide.
4.High enantioselectivities (up to 94 % ee) were attained in the Michael addition of a variety of a,ß -unsaturated imides (1) and malononitrile.
5.Alkylation- Primary aminothiourea derivatives catalyze enantioselective alkylation of a-arylpriopionaldehdyes with diarylbromomethane.
6.Living Ring-Opening Polymerization- A versatile, metal-free, organocatalytic approach to the living ring- opening polymerization of lactide.
7.Neber Reaction- The first enantioselective Neber reaction of ß-ketoxime sulfonates catalyzed by a
bifunctional thiourea.

References

Dynamic Kinetic Resolution of Azlactones by Bifunctional Thioureas with α‑Trifluoromethyl or Methyl Groups

Publication Name: Synlett
Publication Date: 2022-07-29
DOI: 10.1055/a-1892-9911

Activation Modes in Asymmetric Anion-Binding Catalysis

Publication Name: Synthesis
Publication Date: 2022-07-27
DOI: 10.1055/a-1846-6139

Stereoselective Domino Reactions in the Synthesis of Spiro Compounds

Publication Name: Synthesis
Publication Date: 2022-05-16
DOI: 10.1055/a-1771-0641