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692751

Sigma-Aldrich

(R,R)-DACH-pyridyl Trost ligand

95%

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Synonym(s):
(–)-N,N′-(1R,2R)-1,2-Diaminocyclohexanediylbis(2-pyridinecarboxamide)
Empirical Formula (Hill Notation):
C18H20N4O2
CAS Number:
218290-24-5
Molecular Weight:
324.38
MDL number:
MFCD02684543
UNSPSC Code:
12352005
PubChem Substance ID:
329761525
NACRES:
NA.22

Assay

95%

form

solid

optical activity

[α]20/D -97.0°, c = 1 in methanol

mp

171-176 °C

SMILES string

O=C(N[C@@H]1CCCC[C@H]1NC(=O)c2ccccn2)c3ccccn3

InChI

1S/C18H20N4O2/c23-17(15-9-3-5-11-19-15)21-13-7-1-2-8-14(13)22-18(24)16-10-4-6-12-20-16/h3-6,9-14H,1-2,7-8H2,(H,21,23)(H,22,24)/t13-,14-/m1/s1

InChI key

BVYFDUZVVBXFBQ-ZIAGYGMSSA-N

Application

Trost Ligands for Asymmetric Allylic Alkylation
Asymmetric allylic alkylation ligand.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Trost, B.M. et al.
Aldrichimica Acta, 40, 59-59 (2007)
Asymmetric Transition Metal-Catalyzed Allylic Alkylations.
Barry M. Trost et al.
Chemical reviews, 96(1), 395-422 (1996-02-01)
Trost, B.M. et al.
Journal of the American Chemical Society, 124, 11616-11616 (2004)
Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.
Barry M Trost et al.
Chemical reviews, 103(8), 2921-2944 (2003-08-14)

Articles

Trost Ligands for Allylic Alkylation

Trost group pioneers C-2 symmetric ligands for rapid chiral product synthesis in asymmetric catalytic reactions.

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