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692778

Sigma-Aldrich

(R,R)-DACH-naphthyl Trost ligand

95%

Synonym(s):

(1R,2R)-(+)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphino-1-naphthoyl)

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About This Item

Empirical Formula (Hill Notation):
C52H44N2O2P2
CAS Number:
Molecular Weight:
790.87
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

form

powder

optical activity

[α]20/D +69.0°, c = 1 in methanol

mp

224-231 °C

functional group

amide
phosphine

SMILES string

O=C(N[C@@H]1CCCC[C@H]1NC(=O)c2c(ccc3ccccc23)P(c4ccccc4)c5ccccc5)c6c(ccc7ccccc67)P(c8ccccc8)c9ccccc9

InChI

1S/C52H44N2O2P2/c55-51(49-43-29-15-13-19-37(43)33-35-47(49)57(39-21-5-1-6-22-39)40-23-7-2-8-24-40)53-45-31-17-18-32-46(45)54-52(56)50-44-30-16-14-20-38(44)34-36-48(50)58(41-25-9-3-10-26-41)42-27-11-4-12-28-42/h1-16,19-30,33-36,45-46H,17-18,31-32H2,(H,53,55)(H,54,56)/t45-,46-/m1/s1

InChI key

VXFKMKXTPXVEMU-AWSIMMLFSA-N

Application

Asymmetric allylic alkylation ligand.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.
Barry M Trost et al.
Chemical reviews, 103(8), 2921-2944 (2003-08-14)
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)

Articles

Palladium-catalyzed asymmetric allylic alkylation (AAA) has proven to be an exceptionally powerful method for the efficient construction of stereogenic centers.

The Trost group at Stanford University has pioneered the use of C-2 symmetric diaminocyclohexyl (DACH) ligands in AAA, allowing for the rapid synthesis of a diverse range of chiral products with a limited number of chemical transformations.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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