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
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About This Item
Empirical Formula (Hill Notation):
C15H22N2O
CAS Number:
Molecular Weight:
246.35
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Quality Level
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
General description
(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a chiral imidazolidinone organocatalyst, developed by MacMillan and co-workers.
Application
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.
(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.
Features and Benefits
Advantages of MacMillan imidazolidinone organocatalysts:
- 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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Articles
Discover Professor David MacMillan's groundbreaking metal-free asymmetric catalysis using imidazolidinone-based organocatalysts for versatile transformations.
Teresa D Beeson et al.
Science (New York, N.Y.), 316(5824), 582-585 (2007-03-31)
The asymmetric alpha-addition of relatively nonpolar hydrocarbon substrates, such as allyl and aryl groups, to aldehydes and ketones remains a largely unsolved problem in organic synthesis, despite the wide potential utility of direct routes to such products. We reasoned that
The Importance of Iminium Geometry Control in Enamine Catalysis: Identification of a New Catalyst Architecture for Aldehyde-Aldehyde Couplings
Mangion IK, et al.
Angewandte Chemie (International Edition in English), 116(48), 6890-6892 (2004)
Direct asymmetric α-fluorination of aldehydes
Steiner DD, et al.
Angewandte Chemie (International Edition in English), 117(24), 3772-3776 (2005)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 663107-500MG | 04061833473931 |
| 663107-1G | 04061826733349 |