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Sigma-Aldrich

(S,S)-DACH-naphthyl Trost Ligand

95%

Synonym(s):

(1S,2S)-(–)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphino-1-naphthoyl)

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About This Item

Empirical Formula (Hill Notation):
C52H44N2O2P2
CAS Number:
205495-66-5
Molecular Weight:
790.87
MDL number:
MFCD02684552
UNSPSC Code:
12352005
PubChem Substance ID:
329761527
NACRES:
NA.22

Assay

95%

form

solid

optical activity

[α]20/D -66.0°, c = 1 in methanol

mp

232-237 °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-/m0/s1

InChI key

VXFKMKXTPXVEMU-ZYBCLOSLSA-N

Related Categories

Application

Trost Ligands for Asymmetric Allylic Alkylation
Asymmetric allylic alkylation ligand.

Legal Information

Sold in collaboration with Dr. Reddy′s Laboratories for research purposes only.

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

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.

Asymmetric Allylic Alkylation

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

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