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663093

Sigma-Aldrich

(2R,5R)-(+)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone

97%

Synonym(s):

(2R,5R)-2-tert-Butyl-3-methyl-5-phenylmethyl-4-imidazolidinone

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About This Item

Empirical Formula (Hill Notation):
C15H22N2O
CAS Number:
390766-89-9
Molecular Weight:
246.35
MDL number:
MFCD08276842
UNSPSC Code:
12352005
PubChem Substance ID:
24884184
NACRES:
NA.22

Assay

97%

form

solid

mp

93-100 °C

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-/m1/s1

InChI key

SKHPYKHVYFTIOI-TZMCWYRMSA-N

General description

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

Application

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL6145
MKCD7805
MKBP3243V
08608KJ
01511PD

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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
Stéphane G Ouellet et al.
Journal of the American Chemical Society, 127(1), 32-33 (2005-01-06)
The first enantioselective organocatalytic hydride reduction has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of beta,beta-substituted alpha,beta-unsaturated aldehydes to generate beta-stereogenic aldehydes. The use of imidazolidinone 2 as the asymmetric
Modern strategies in organic catalysis: the advent and development of iminium activation.
Lelais G and MacMillan DWC.
Aldrichimica Acta, 39(3), 79-87 (2006)

Articles

Macmillan Imidazolidinone Organocatalysts

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

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