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665290

Sigma-Aldrich

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

97%

Synonym(s):

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

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About This Item

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

Quality Level

Assay

97%

form

solid

mp

88-89 °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-/m0/s1

InChI key

LKZPDRCMCSBQFN-UIOOFZCWSA-N

Application

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.
The product may be used as a ligand in:
  • Iridium-catalyzed allylic etherification of acyclic, achiral allylic carbonates with potassium silanolates to form chiral allylic alcohols.
  • Palladium-catalyzed asymmetric allylic cyclisation of N-tosyl and N-benzyl carbonates to form the corresponding pyrrolidine and piperidine derivatives, respectively.
  • Intramolecular iridium-catalyzed allylic cyclizationof (E)-allylic methyl carbonates to form 2,5-trans/cis pyrrolidine derivatives.

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

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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Enantioselective synthesis of N-heterocycles via intramolecular Pd (0)-catalysed allylic amination.
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Asymmetric synthesis of 2, 5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations.
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Privileged Ligands
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Articles

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

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

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

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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