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Key Documents

ALD00378

Sigma-Aldrich

Wasa-Yu MPAA Ligand

Synonym(s):

(S)-3-(2,6-Difluorophenyl)-2-((((4-(trichloromethyl)heptan-4- yl)oxy)carbonyl)amino)propanoic acid

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About This Item

Empirical Formula (Hill Notation):
C18H22Cl3F2NO4
CAS Number:
Molecular Weight:
460.73
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

form

solid

reaction suitability

reaction type: C-H Activation
reagent type: catalyst
reagent type: ligand
reaction type: Peptide Synthesis

bp

521.1 °C±50.0 °C

density

1.365 g/cm3±0.06 g/cm3

functional group

amine
carboxylic acid

storage temp.

2-8°C

SMILES string

O=C(O)[C@@H](NC(OC(CCC)(CCC)C(Cl)(Cl)Cl)=O)CC1=C(F)C=CC=C1F

InChI

1S/C18H22Cl3F2NO4/c1-3-8-17(9-4-2,18(19,20)21)28-16(27)24-14(15(25)26)10-11-12(22)6-5-7-13(11)23/h5-7,14H,3-4,8-10H2,1-2H3,(H,24,27)(H,25,26)/t14-/m0/s1

InChI key

MYNBDMWXOQDYED-AWEZNQCLSA-N

Application

The Wasa-Yu MPAA Ligand has been reported by Yu and coworkers to promote the enantioselective C-H activation of cyclopropanes. This transformation is carried out through the coupling of organoboron reagents using palladium-mediated catalysis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Related Content

The Yu program centers around the discovery of catalytic carbon–carbon and carbon–heteroatom bond forming reactions based on C–H activation. Target transformations are selected to enable 1) the use of simple and abundant starting materials such as aliphatic acids, amines and alcohols, and 2) disconnections that drastically shorten the synthesis of a drug molecule or a major class of biologically active compounds.

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