Skip to Content
Merck
CN

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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C15H22N2O
CAS Number:
346440-54-8
Molecular Weight:
246.35
NACRES:
NA.22
PubChem Substance ID:
24884185
UNSPSC Code:
12352005
MDL number:
MFCD03426982

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

(2S,5S)-(−)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone, 97%

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

SMILES string

CN1[C@H](N[C@@H](Cc2ccccc2)C1=O)C(C)(C)C

InChI key

SKHPYKHVYFTIOI-JSGCOSHPSA-N

assay

97%

form

solid

mp

93-100 °C (lit.)

functional group

phenyl

Quality Level

100

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCL0239
MKCB9631
MKCC0040
MKBR2222V
MKBL8730V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Asymmetric organocatalysis of 4+ 3 cycloaddition reactions
Harmata M, et al.
Journal of the American Chemical Society, 125(8), 2058-2059 (2003)
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)
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)
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
View All Related Papers

Articles

Macmillan Imidazolidinone Organocatalysts

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service