Skip to Content
Merck
All Photos(2)

Documents

692778

Sigma-Aldrich

(R,R)-DACH-naphthyl Trost ligand

95%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C52H44N2O2P2
CAS Number:
174810-09-4
Molecular Weight:
790.87
MDL number:
MFCD02684551
UNSPSC Code:
12352005
PubChem Substance ID:
329761526
NACRES:
NA.22

Assay

95%

form

powder

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

Application

Trost Ligands for Asymmetric Allylic Alkylation
Asymmetric allylic alkylation ligand.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

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 for Asymmetric Allylic Alkylation

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.

Contact Technical Service