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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

Quality Level

100

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)

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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Asymmetric Copper-Catalyzed C (sp)-H Bond Insertion of Carbenoids Derived from N-Tosylhydrazones
Osako T, et al.
Synlett, 29(17), 2251-2256 (2018)
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)
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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