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692794

Sigma-Aldrich

(S,S)-DACH-phenyl Trost ligand

95%

Synonym(s):
(1S,2S)-(–)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphinobenzoyl)
Empirical Formula (Hill Notation):
C44H40N2O2P2
CAS Number:
Molecular Weight:
690.75
MDL number:
PubChem Substance ID:

assay

95%

form

solid

optical activity

[α]20/D -134°, 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-/m0/s1

InChI key

AXMSEDAJMGFTLR-ZAQUEYBZSA-N

Application

Asymmetric allylic alkylation ligand.

Packaging

1 g in glass bottle
250 mg in glass bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Legal Information

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More documents

Quotes and Ordering

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

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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