663107

(2S,5S)-(−)-2-tert-Butyl-3-methyl-5-benzyl-4-Imidazolidinon

97%

• Synonym(e): (2S,5S)-2-tert-Butyl-3-methyl-5-phenylmethyl-4-imidazolidinon, (2S,5S)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinon
• Empirische Formel (Hill-System): C₁₅H₂₂N₂O
• CAS-Nummer: 346440-54-8
• Molekulargewicht: 246.35
• MDL-Nummer: MFCD03426982
• UNSPSC-Code: 12352005
• PubChem Substanz-ID: 24884185
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 100
• Assay: 97%
• Form: solid
• mp (Schmelzpunkt): 93-100 °C (lit.)
• Funktionelle Gruppe: phenyl
• SMILES String: CN1[C@H](N[C@@H](Cc2ccccc2)C1=O)C(C)(C)C
• InChI: 1S/C15H22N2O/c1-15(2,3)14-16-12(13(18)17(14)4)10-11-8-6-5-7-9-11/h5-9,12,14,16H,10H2,1-4H3/t12-,14-/m0/s1
• InChIKey: SKHPYKHVYFTIOI-JSGCOSHPSA-N

Beschreibung

Allgemeine Beschreibung

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a chiral imidazolidinone organocatalyst, developed by MacMillan and co-workers.

Anwendung

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a second-generation MacMillan catalyst, which can be used as a chiral organocatalyst in:

• The chiral transformation reaction, including Friedel-Crafts and Mukaiyama-Michael reactions.
• The preparation of substituted spiroundecenetriones via asymmetric domino Knoevenagel/Diels-Alder reactions.
• The asymmetric synthesis of β-hydroxy aldehydes and their dimethylacetals via aldehyde-aldehyde aldol condensation reaction.
• The enantioselective α-fluorination of aldehydes using N-fluorobenzenesulfonamide as a fluorinating agent.
• The stereoselective preparation of (oxomethyl)oxabicyclo[3.2.1]octenones and tricyclic pyrroles via [4+3] cycloaddition of (trialkylsiloxy)pentadienals to furans.

Metal-free OrganoCatalyst^™ technology for asymmetric catalysis. Catalyzes asymmetric indole alkylations, Friedel-Crafts alkylations, and a broad range of conjugate addition reactions in high enantiomeric excess.

Leistungsmerkmale und Vorteile

Advantages of MacMillan imidazolidinone organocatalysts:

• Superior enantiocontrol in numerous transformations
• High activities at low catalyst loadings
• Extraordinary functional group tolerance

Rechtliche Hinweise

U.S. Pat. 6,369,243 and related patents apply. For research purposes only.

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)