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  • 663107 - (2S,5S)-(−)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone

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663107 Sigma-Aldrich

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

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

  •  PubChem Substance ID 24884185

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, MacMillan Imidazolidinone OrganoCatalysts
assay   97%
mp   93-100 °C (lit.)
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.

Packaging

1 g in glass bottle

500 mg in glass insert

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.

Used in the 1,4-addition of electron-rich benzenes to unsaturated aldehydes, asymmetric hydride reduction of α,β-unsaturated aldehydes, and α-functionalization of aldehydes.

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Chemfiles Volume 6 Article | MacMillan Imidazolidinone OrganoCatalysts™

Developed by Professor David MacMillan at Caltech, imidazolidinonebased organocatalysts are designed to serve as general catalysts for a myriad of asymmetric transformations. The first highly enantio...
Chemfiles Volume 6 Article 4
Keywords: Alkylations, Asymmetric synthesis, Catalysis, Chemfiles, Chlorinations, Condensations, Cycloadditions, Drug discovery, Fluorinations, Halogenations, Hydrogenations

Related Content

Macmillan Imidazolidinone Organocatalysts in Chemical Sythesis

Developed by Professor David MacMillan at Caltech, imidazolidinone-based OrganoCatalysts are designed to serve as general catalysts for a variety of asymmetric transformations. The first highly enant...
Keywords: Alkylations, Asymmetric catalysis, Asymmetric synthesis, Catalysis, Chlorinations, Condensations, Cycloadditions, Diels-Alder reaction, Fluorinations, Friedel-Crafts Alkylation

Peer-Reviewed Papers
15

References

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