All Photos(2)

692778

Sigma-Aldrich

(R,R)-DACH-naphthyl Trost ligand

95%

Synonym(s):
(1R,2R)-(+)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphino-1-naphthoyl)
Empirical Formula (Hill Notation):
C52H44N2O2P2
CAS Number:
Molecular Weight:
790.87
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

optical activity

[α]20/D +69.0°, c = 1 in methanol

mp

224-231 °C

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

Related Categories

Application

Asymmetric allylic alkylation ligand.

Packaging

1 g in glass bottle
250 mg in amber glass bottle

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Trost, B.M. et al.
Aldrichimica Acta, 40, 59-59 (2007)
Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis.
Barry M Trost et al.
Chemical reviews, 103(8), 2921-2944 (2003-08-14)
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

Asymmetric Allylic Alkylation

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

Trost Ligands

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.

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