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665355

Sigma-Aldrich

(S)-(+)-Benzyl(3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a′]dinaphthalen-4-yl)methylamine

97%

Synonym(s):

(+)-N-Benzyl-N-methyl-dinaphtho[2,1-d:1′,2′]dioxaphosphepin-4-amine, (11bS)

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About This Item

Empirical Formula (Hill Notation):
C28H22NO2P
CAS Number:
490023-37-5
Molecular Weight:
435.45
MDL number:
MFCD04117686
UNSPSC Code:
12352005
PubChem Substance ID:
24884732
NACRES:
NA.22

Assay

97%

form

solid

mp

155-159 °C

SMILES string

CN(Cc1ccccc1)P2Oc3ccc4ccccc4c3-c5c(O2)ccc6ccccc56

InChI

1S/C28H22NO2P/c1-29(19-20-9-3-2-4-10-20)32-30-25-17-15-21-11-5-7-13-23(21)27(25)28-24-14-8-6-12-22(24)16-18-26(28)31-32/h2-18H,19H2,1H3

InChI key

OHGGHRJGBXAKKY-UHFFFAOYSA-N

Related Categories

Application

DSM MonoPhos Family of Highly Efficient Privileged Ligands
Phosphoramidite ligand used in a rhodium-catalyzed enantioselective 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds. Also used in asymmetric hydrogenation of N-acylated β-dehydroamino esters to enantiopure β-amino acid derivatives.

Legal Information

Sold under license from DSM for research purposes only.

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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Certificates of Analysis (COA)

Lot/Batch Number
01503CE

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Diego Peña et al.
Journal of the American Chemical Society, 124(49), 14552-14553 (2002-12-06)
New and very easily accessible monodentate phosphoramidite ligands have been developed that lead to excellent ee's and full conversions in the hydrogenation of (E)- and (Z)-beta-dehydroamino acid derivatives with both aliphatic and aromatic side chains. Particularly, two different catalytic systems
Journal of Organometallic Chemistry, 692, 428-428 (2007)

Articles

DSM MonoPhos™ Ligands

DSM MonoPhos™ Ligands

DSM MonoPhos Family

A diverse array of these chiral, monodentate phosphoramidites based on the privileged BINOL platform. The MonoPhos™ family has exhibited high levels of enantiocontrol in synthetic transformations ranging from metal-catalyzed asymmetric 1,4-additions of organometallic reagents to allylic alkylations to desymmetrization of meso-cycloalkene oxides.

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