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Sigma-Aldrich

(2R,2R′,3R,3R′)-WingPhos

greener alternative

Synonym(s):

(2R,2′R,3R,3′R)-4,4′-Di(anthracen-9-yl)-3,3′-di-tert-butyl-2,2′,3,3′-tetrahydro-2,2′-bibenzo[d][1,3]oxaphosphole

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About This Item

Empirical Formula (Hill Notation):
C50H44O2P2
CAS Number:
1884680-45-8
Molecular Weight:
738.83
UNSPSC Code:
12352200

form

powder or crystals

optical purity

ee: ≥99% (HPLC)

reaction suitability

reagent type: ligand

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

functional group

phosphine

greener alternative category

Aligned,

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

(2R,2R′,3R,3R′)-WingPhos is a P-chiral biphosphorus ligand for Rh-catalyzed asymmetric hydrogenations as well as Rh-catalyzed asymmetric addition of aryl boroxines to ketones.

Product can be used with our benchtop hydrogen generator, H-Genie Lite (Z744083)

Other Notes

Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to N-Unprotected Ketimines: Efficient Synthesis of Cipargamin

Legal Information

Sold in collaboration with Zejun Pharmaceuticals

Storage Class Code

11 - Combustible Solids

WGK

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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Linwei Huang et al.
Angewandte Chemie (International ed. in English), 55(14), 4527-4531 (2016-03-05)
Highly enantioselective additions of arylboroxines to simple aryl ketones have been achieved for the first time with a Rh/(R,R,R,R)-WingPhos catalyst, thus providing a range of chiral diaryl alkyl carbinols with excellent ee values and yields. (R,R,R,R)-WingPhos has been proven to be
Jinbin Zhu et al.
Angewandte Chemie (International ed. in English), 58(45), 16119-16123 (2019-08-31)
Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-unprotected ketimines is realized for the first time by employing chiral BIBOP-type ligands with a Rh loading as low as 1 mol %. A range of chiral α-trifluoromethyl-α,α-diaryl α-tertiary amines or 3-amino-3-aryloxindoles were formed with

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