663107

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

97%

• Synonym(s): (2S,5S)-2-tert-Butyl-3-methyl-5-phenylmethyl-4-imidazolidinone, (2S,5S)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone
• Empirical Formula (Hill Notation): C₁₅H₂₂N₂O
• CAS Number: 346440-54-8
• Molecular Weight: 246.35
• MDL number: MFCD03426982
• UNSPSC Code: 12352005
• PubChem Substance ID: 24884185
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 97%
• form: solid
• mp: 93-100 °C (lit.)
• functional group: 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
• InChI key: SKHPYKHVYFTIOI-JSGCOSHPSA-N

Description

General description

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a chiral imidazolidinone organocatalyst, developed by MacMillan and co-workers.[1]

Application

(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.[2]
• The preparation of substituted spiroundecenetriones via asymmetric domino Knoevenagel/Diels-Alder reactions.[3]
• The asymmetric synthesis of β-hydroxy aldehydes and their dimethylacetals via aldehyde-aldehyde aldol condensation reaction.[4]
• The enantioselective α-fluorination of aldehydes using N-fluorobenzenesulfonamide as a fluorinating agent.[5]
• The stereoselective preparation of (oxomethyl)oxabicyclo[3.2.1]octenones and tricyclic pyrroles via [4+3] cycloaddition of (trialkylsiloxy)pentadienals to furans.[6]

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.

Features and Benefits

Advantages of MacMillan imidazolidinone organocatalysts:[1]

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

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)