Key Documents

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

NACRES:

NA.22

PubChem Substance ID:

24884726

UNSPSC Code:

12352005

MDL number:

MFCD04117688

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Properties

Quality Level

100

assay

97%

form

solid

mp

88-89 °C

functional group

amine, phenyl

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

Description

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.

DSM MonoPhos Family of Highly Efficient Privileged Ligands

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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.

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)

View All Related Papers

Global Trade Item Number

SKU	GTIN
665290-100MG	04061832623900
665290-500MG	04061832623924
665290-2G	04061832623917