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

ALDRICH/663107 - 97%

Synonym: (2S,5S)-2-tert-Butyl-3-methyl-5-phenylmethyl-4-imidazolidinone; (2S,5S)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone

CAS Number: 346440-54-8
Empirical Formula (Hill Notation): C₁₅H₂₂N₂O
Molecular Weight: 246.35
MDL Number: MFCD03426982
Linear Formula: C₁₅H₂₂N₂O
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-663107-500MG	500 mg	$265.00 1/EA	Add To Favorites
45-663107-1G	1 g	$456.00 1/EA	Add To Favorites

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 663107-500MG.

Properties
Descriptions
Safety Info.
Basic Data

assay	97%
form	solid
functional group	phenyl
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
mp	93-100 °C (lit.)
Quality Level	100
SMILES string	CN1[C@H](N[C@@H](Cc2ccccc2)C1=O)C(C)(C)C

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. • 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.
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.
Features and Benefits:	Advantages of MacMillan imidazolidinone organocatalysts: • Superior enantiocontrol in numerous transformations • High activities at low catalyst loadings • Extraordinary functional group tolerance
General description:	(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a chiral imidazolidinone organocatalyst, developed by MacMillan and co-workers.
Legal Information:	U.S. Pat. 6,369,243 and related patents apply. For research purposes only.
Packaging:	1 g in glass bottle
Packaging:	500 mg in glass insert

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	97%
mp	93-100 °C (lit.)
UNSPSC	12352005

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