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663107

Sigma-Aldrich

(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:
346440-54-8
Molecular Weight:
246.35
MDL number:
MFCD03426982
UNSPSC Code:
12352005
PubChem Substance ID:
24884185
NACRES:
NA.22

assay

97%

form

solid

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

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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

(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.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Evaluation of protonation sites in two MacMillan catalysts in solution by gas phase predissociation spectroscopy and electronic structure calculations
Tavares LC, et al.
Organic Chemistry, 134-145 (2020)
Nick A Paras et al.
Journal of the American Chemical Society, 124(27), 7894-7895 (2002-07-04)
The first enantioselective organocatalytic alkylation of electron-rich benzene rings with alpha,beta-unsaturated aldehydes has been accomplished. The use of iminium catalysis has provided a new strategy for the enantioselective construction of benzylic stereogenicity, an important chiral synthon for natural product and
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Macmillan Imidazolidinone Organocatalysts

Discover Professor David MacMillan's groundbreaking metal-free asymmetric catalysis using imidazolidinone-based organocatalysts for versatile transformations.

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