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678635

Sigma-Aldrich

1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene monooxide

kanata purity

Synonym(s):

(2R,5R)-1-{2-[(2R,5R)-2,5-Dimethylphospholan-1-yl]phenyl}-2,5-dimethylphospholane 1-oxide, R,R-Me-BozPhos

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About This Item

Empirical Formula (Hill Notation):
C18H28OP2
CAS Number:
638132-66-8
Molecular Weight:
322.36
MDL number:
MFCD09750450
UNSPSC Code:
12352005
PubChem Substance ID:
24885440
NACRES:
NA.22

form

solid

optical activity

[α]22/D -171°, c = 1 in chloroform

mp

116-122 °C

SMILES string

C[C@@H]1CC[C@@H](C)P1(C2=CC=CC=C2P3[C@H](C)CC[C@H]3C)=O

InChI

1S/C18H28OP2/c1-13-9-10-14(2)20(13)17-7-5-6-8-18(17)21(19)15(3)11-12-16(21)4/h5-8,13-16H,9-12H2,1-4H3/t13-,14-,15-,16-/m1/s1

InChI key

ORZVYNTUPREFTI-KLHDSHLOSA-N

General description

1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene monooxide is a chiral ligand whose copper complexes are used extensively in many organic reactions such as addition to imines, nitroalkenes, and reduction of β,β-disubstituted vinyl sulfones.

Application

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands
1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene monoxide can be used:
  • As a ligand in the preparation of dihydroquinolones and dihydroisoquinolones through palladium-catalyzed C-H functionalization of cyclopropane derivatives.
  • As an organocatalyst in the [4+1] annulation reactions of 2-enoylpyridine pyridine N-oxides and olefins with Morita-Baylis-Hillman (MBH) carbonates to yield dihydrofurans derivatives enantioselectively.
  • As a ligand in the copper-catalyzed synthesis of chiral nitroalkanes via the addition of dialkylzinc to β-nitroalkenes.

Legal Information

Sold in collaboration with Kanata Chemical Technologies Inc. for research purposes only. These compounds were made and sold under license from E.I. du Pont de Nemours and Company, which license does not include the right to use the compounds in producing products for sale in the pharmaceutical field.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Utilization of BozPhos as an Effective Ligand in Enantioselective C-H Functionalization of Cyclopropanes: Synthesis of Dihydroisoquinolones and Dihydroquinolones
Mayer C, et al.
Organic Letters, 21(8), 2639-2644 (2019)
Application of the chiral bis (phosphine) monoxide ligand to catalytic enantioselective addition of dialkylzinc reagents to β-Nitroalkenes
Cote A, et al.
Organic Letters, 9(1), 85-87 (2007)
(R,R)?Me?DuPHOS Monoxide
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2011)
Organocatalytic enantioselective [1+ 4] annulation of Morita-Baylis-Hillman carbonates with electron-deficient olefins: Access to chiral 2, 3-dihydrofuran derivatives
Cheng Y, et al.
Organic Letters, 19(18), 4774-4777 (2017)
Enantioselective Construction of Pyridine N-Oxides Featuring 2, 3-Dihydrofuran Motifs via Phosphine-Catalyzed [4+ 1]-Annulation of 2-Enoylpyridine N-Oxides with Morita-Baylis-Hillman Carbonates
Zhang P, et al.
Organic Letters, 21(1), 152-155 (2018)

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