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685569

Sigma-Aldrich

(11bS)-N,N-dimethyl-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine

Synonym(s):

MonoPhos Ligand

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About This Item

Empirical Formula (Hill Notation):
C22H26NO2P
CAS Number:
389130-06-7
Molecular Weight:
367.42
MDL number:
MFCD04117692
UNSPSC Code:
12352005
PubChem Substance ID:
329760980
NACRES:
NA.22

form

solid

optical activity

[α]22/D 282.0°, c = 1 in chloroform

mp

86-94 °C

SMILES string

CN(C)P1Oc2ccc3CCCCc3c2-c4c(O1)ccc5CCCCc45

InChI

1S/C22H26NO2P/c1-23(2)26-24-19-13-11-15-7-3-5-9-17(15)21(19)22-18-10-6-4-8-16(18)12-14-20(22)25-26/h11-14H,3-10H2,1-2H3

InChI key

OIZQADYWBXZQKE-UHFFFAOYSA-N

Related Categories

Application

DSM MonoPhos Family of Highly Efficient Privileged Ligands
(11bS)-N,N-dimethyl-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine is a monodentate phosphoramidite (MonoPhos) chiral ligand that can be used:
  • In the Cu-catalyzed synthesis of chiral 3-(arylbut-1-yn-1-yl)silane derivatives by reacting N-tosylhydrazones with silyl-substituted alkynes via asymmetric insertion.
  • In the Rh-catalyzed asymmetric hydrogenation of R-isopropylcinnamic acid derivative, a key intermediate of renin inhibitor aliskiren.
  • In the Rh-catalyzed conjugate addition of arylboronic acids to lactones, enones, and nitroalkenes.

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

Certificates of Analysis (COA)

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A mixed-ligand approach enables the asymmetric hydrogenation of an α-isopropylcinnamic acid en route to the renin inhibitor aliskiren
Boogers JAF, et al.
Organic Process Research & Development, 11(3), 585-591 (2007)
Asymmetric Copper-Catalyzed C (sp)-H Bond Insertion of Carbenoids Derived from N-Tosylhydrazones
Osako T, et al.
Synlett, 29(17), 2251-2256 (2018)
Rhodium-catalyzed asymmetric conjugate additions of boronic acids using monodentate phosphoramidite ligands
Boiteau J, et al.
Organic Letters, 5(5), 681-684 (2003)

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