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Sigma-Aldrich

(R,R)-DACH-phenyl Trost ligand

95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C44H40N2O2P2
CAS Number:
138517-61-0
Molecular Weight:
690.75
MDL number:
MFCD01631273
UNSPSC Code:
12352002
PubChem Substance ID:
329761529
NACRES:
NA.22

Assay

95%

form

solid

optical activity

[α]20/D +131°, c = 1 in methanol

mp

136-142 °C

SMILES string

O=C(N[C@@H]1CCCC[C@H]1NC(=O)c2ccccc2P(c3ccccc3)c4ccccc4)c5ccccc5P(c6ccccc6)c7ccccc7

InChI

1S/C44H40N2O2P2/c47-43(37-27-13-17-31-41(37)49(33-19-5-1-6-20-33)34-21-7-2-8-22-34)45-39-29-15-16-30-40(39)46-44(48)38-28-14-18-32-42(38)50(35-23-9-3-10-24-35)36-25-11-4-12-26-36/h1-14,17-28,31-32,39-40H,15-16,29-30H2,(H,45,47)(H,46,48)/t39-,40-/m1/s1

InChI key

AXMSEDAJMGFTLR-XRSDMRJBSA-N

Related Categories

Application

Trost Ligands for Asymmetric Allylic Alkylation
Asymmetirc allylic alkylation ligand.

Legal Information

Sold in collaboration with Dr. Reddy′s Laboratories for research purposes only. US Patent 5739396 applies.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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

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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