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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

functional group

phosphine oxide
phosphine

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
02205DH

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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)
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)
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)
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)
(R,R)?Me?DuPHOS Monoxide
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2011)

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