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663077

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

Name: (5<I>R</I>)-(+)-2,2,3-Trimethyl-5-benzyl-4-imidazolidinone dichloroacetic acid
Brand: ALDRICH

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

NACRES:

NA.22

PubChem Substance ID:

24884182

UNSPSC Code:

12352005

MDL number:

MFCD08276840

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Properties

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

Description

Application

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

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)

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Articles

Macmillan Imidazolidinone Organocatalysts

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

Enantioselective organocatalytic alpha-fluorination of aldehydes

Beeson TD and MacMillan DWC

Journal of the American Chemical Society, 127(24), 8826-8828 (2005)

Enantioselective organocatalytic alpha-fluorination of aldehydes.

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.

Enantiomeric impurities in chiral catalysts, auxiliaries, and synthons used in enantioselective syntheses. Part 5

Thakur N, et al.

Chirality, 31(9), 688-699 (2019)

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Global Trade Item Number

SKU	GTIN
663077-500MG	04061833473917
663077-2G	04061833549131