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Merck
CN

ALD00376

Sigma-Aldrich

Shi-Yu MPAA Ligand

Synonym(s):

N-[[[(1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl]oxy]carbonyl]-L-leucine

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About This Item

Empirical Formula (Hill Notation):
C17H31NO4
CAS Number:
1047650-54-3
Molecular Weight:
313.43
UNSPSC Code:
12352108
PubChem Substance ID:
329772659
NACRES:
NA.22

Key Documents

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form

solid

reaction suitability

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

functional group

amine
carboxylic acid

storage temp.

2-8°C

SMILES string

O=C(O)[C@@H](NC(O[C@H]1[C@H](C(C)C)CC[C@@H](C)C1)=O)CC(C)C

InChI

1S/C17H31NO4/c1-10(2)8-14(16(19)20)18-17(21)22-15-9-12(5)6-7-13(15)11(3)4/h10-15H,6-9H2,1-5H3,(H,18,21)(H,19,20)/t12-,13+,14+,15-/m1/s1

InChI key

JDNKQMWGCKCHBF-CBBWQLFWSA-N

Application

Shi-Yu MPAA Ligand is a monoprotected α-amino acid that can be used as an effective chiral ligand in the asymmetric palladium-catalyzed alkylation reactions. It is also utilized in the alkylation of diphenyl(2-pyridyl)methane and isopropyl pyridines with alkyl boronic acids via enantioselective activation of C(sp2)-H and C(sp3)-H bonds, respectively.
The Shi-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.

Other Notes

Pd(II)-Catalyzed Enantioselective C–H Activation of Cyclopropanes

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Pd(II)-catalyzed enantioselective activation of C(sp2)-H and C(sp3)-H bonds using monoprotected amino acids as chiral ligands.
Bing-Feng Shi et al.
Angewandte Chemie (International ed. in English), 47(26), 4882-4886 (2008-05-20)

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