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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)

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Synonym(s):
(+)-N,N-Bis[(1R)-1-phenylethyl]-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine, (11bS)
Empirical Formula (Hill Notation):
C36H30NO2P
CAS Number:
497883-22-4
Molecular Weight:
539.60
MDL number:
MFCD08561138
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

Related Categories

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 Code

11 - 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

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Organic & Biomolecular Chemistry, 4, 1278-1278 (2006)
Privileged Ligands
Aldrich Chemfiles, 6(8), 7-7 null
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

In collaboration with DSM, we are pleased to offer a range of MonoPhos™ ligands for the research market.† Feringa and co-workers have invented a diverse array of these chiral, monodentate phosphoramidites based on the privileged BINOL platform.

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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