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663077

Sigma-Aldrich

(5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone dichloroacetic acid

97%

Synonym(s):

(5R)-2,2,3-Trimethyl-5-phenylmethyl-4-imidazolidinone dichloroacetic acid

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About This Item

Empirical Formula (Hill Notation):
C15H20Cl2N2O3
CAS Number:
857303-87-8
Molecular Weight:
347.24
MDL number:
MFCD08276840
UNSPSC Code:
12352005
PubChem Substance ID:
24884182
NACRES:
NA.22

assay

97%

form

solid

mp

122-126 °C

functional group

carboxylic acid
chloro
phenyl

SMILES string

OC(=O)C(Cl)Cl.CN1C(=O)[C@@H](Cc2ccccc2)NC1(C)C

InChI

1S/C13H18N2O.C2H2Cl2O2/c1-13(2)14-11(12(16)15(13)3)9-10-7-5-4-6-8-10;3-1(4)2(5)6/h4-8,11,14H,9H2,1-3H3;1H,(H,5,6)/t11-;/m1./s1

InChI key

YZRAPAXOLQHZSE-RFVHGSKJSA-N

Application

(5R)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone dichloroacetic acid is a Macmillan imidazolidinone organocatalyst[1] that can be used in the enantioselective organocatalytic α-fluorination of aldehydes[2] and cyclic ketones.[3]

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)

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Certificates of Analysis (COA)

Lot/Batch Number
MKBV4548V
MKBG1811V
12707CJ
15003MD

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Enantioselective organocatalytic alpha-fluorination of aldehydes
Beeson TD and MacMillan DWC
Journal of the American Chemical Society, 127(24), 8826-8828 (2005)
Enantiomeric impurities in chiral catalysts, auxiliaries, and synthons used in enantioselective syntheses. Part 5
Thakur N, et al.
Chirality, 31(9), 688-699 (2019)
Teresa D Beeson et al.
Journal of the American Chemical Society, 127(24), 8826-8828 (2005-06-16)
The first direct enantioselective catalytic alpha-fluorination of aldehydes has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective fluorination of aldehydes to generate alpha-fluoro aldehydes, an important chiral synthon for medicinal agent synthesis.
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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