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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

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

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:

380230-02-4

Molecular Weight:

539.60

MDL number:

MFCD04117688

UNSPSC Code:

12352005

PubChem Substance ID:

24884726

NACRES:

NA.22

Quality Level

100

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

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Chiral Catalysts & Ligands

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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.

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.

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.

Olszewska B, et al.

Tetrahedron, 69(46), 9551-9556 (2013)

Marcovic', D.; Hartwig, J. F.

Journal of the American Chemical Society, 129 (2007)

Asymmetric synthesis of 2, 5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations.

Natori Y, et al.

Organic & Biomolecular Chemistry, 12(12), 1983-1994 (2014)

Privileged Ligands

Aldrich Chemfiles, 6(8), 7-7 null

Organic & Biomolecular Chemistry, 4, 1278-1278 (2006)

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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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