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  • 665290 - (S,S,S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a’]dinaphthalen-4-yl)bis(1-phenylethyl)amine

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

  • CAS Number 380230-02-4

  • Empirical Formula (Hill Notation) C36H30NO2P

  • Molecular Weight 539.60

  •  MDL number MFCD04117688

  •  PubChem Substance ID 24884726

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, DSM MonoPhos Phosphoramidites, Privileged Ligands and Complexes More...
InChI Key   LKZPDRCMCSBQFN-UIOOFZCWSA-N
assay   97%
mp   88-89 °C

Description

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.

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.

Packaging

100, 500 mg in glass insert

2 g in glass bottle

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.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

DSM MonoPhos™ Family - Highly Efficient Privileged Ligands

Feringa and co-workers have invented a diverse array of chiral, monodentate phosphoramidites based on the privileged BINOL platform.1 The MonoPhos™ family has exhibited high levels of enantiocontrol ...
Aldrich ChemFiles 2006, 6.4, 15.
Keywords: Addition reactions, Alkylations, Asymmetric synthesis, Catalysis, Chemfiles, Desymmetrizations, Hydrogenations, Ligands

DSM MonoPhos™

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 phosphorami...
ChemFiles 2006, 6.8, 7.
Keywords: Addition reactions, Alkylations, Aminations, Annulations, Asymmetric synthesis, Building blocks, Catalysis, Cyclizations, Desymmetrizations, Drug discovery, Hydrogenations, Infrared spectroscopy, Ligands, Organic synthesis, Oxidations, Substitutions

Related Content

DSM MonoPhos Family- Highly Efficient Privileged Ligands

In collaboration with DSM, we are pleased to offer a range of MonoPhos™ ligands to the research market.† Feringa and co-workers have invented a diverse array of these chiral, monodentate phosphoramid...
Keywords: Addition reactions, Alkylations, Aminations, Annulations, Asymmetric synthesis, Building blocks, Catalysis, Cyclizations, Desymmetrizations, Drug discovery, Hydrogenations, Infrared spectroscopy, Ligands, Organic synthesis, Oxidations, Substitutions

Peer-Reviewed Papers
15

References

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