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665363

Sigma-Aldrich

(S,R,R)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a′]dinaphthalen-4-yl)bis(1-phenylethyl)amine

95% (HPLC)

Synonym(s):

(+)-N,N-Bis[(1R)-1-phenylethyl]-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, (11bS)

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About This Item

Empirical Formula (Hill Notation):
C36H30NO2P
CAS Number:
497883-22-4
Molecular Weight:
539.60
MDL number:
MFCD08561138
UNSPSC Code:
12352005
PubChem Substance ID:
24884733
NACRES:
NA.22

Quality Level

100

assay

95% (HPLC)

mp

102-103 °C

SMILES string

C[C@@H](N([C@H](C)c1ccccc1)P2Oc3ccc4ccccc4c3-c5c(O2)ccc6ccccc56)c7ccccc7

InChI

1S/C36H30NO2P/c1-25(27-13-5-3-6-14-27)37(26(2)28-15-7-4-8-16-28)40-38-33-23-21-29-17-9-11-19-31(29)35(33)36-32-20-12-10-18-30(32)22-24-34(36)39-40/h3-26H,1-2H3/t25-,26-/m1/s1

InChI key

LKZPDRCMCSBQFN-CLJLJLNGSA-N

Application

DSM MonoPhos Family of Highly Efficient Privileged Ligands
Chiral phosphoramidite ligand used in a highly enantioselective copper-catalyzed conjugate addition of diakylzincs to a variety of Michael acceptors. Also used in a palladium-catalyzed diethylzinc mediated umpolung allylation.

Features and Benefits

Advantages of the MonoPhos® ligands:
  • Superior enantiocontrol in numerous transformations
  • High activities at low catalyst loadings
  • Hydrogenations under low-pressure conditions

Legal Information

Sold under license from DSM for research purposes only.
MonoPhos is a registered trademark of DSM IP Assets B.V.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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’.

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Privileged Ligands
Aldrich Chemfiles, 6(8), 7-7 null
Organic & Biomolecular Chemistry, 4, 1278-1278 (2006)
Oliver Knopff et al.
Organic letters, 4(22), 3835-3837 (2003-02-26)
[formula: see text] The zinc enolates, resulting from the copper-catalyzed enantioselective conjugate addition of dialkyl zinc reagents to cyclic and acyclic enones, could be trapped, quantitatively, as silyl enol ethers with TMSOTf in apolar solvents or with TMSCI and NEt3.
Synlett, 1375-1375 (2001)
Jorge Esquivias et al.
The Journal of organic chemistry, 70(18), 7451-7454 (2005-08-27)
[reaction: see text] The enantioselective catalytic 1,4-addition to alpha,beta-unsaturated ketimines is an unprecedented process. Herein, we document the copper-catalyzed addition of dialkylzinc reagents to (2-pyridylsulfonyl)imines of chalcones. This process occurs rapidly in the presence of a chiral phosphoramidite ligand to

Articles

DSM MonoPhos™ Ligands

DSM collaboration offers MonoPhos™ ligands for research, based on the BINOL platform by Feringa and co-workers.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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