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913200

Sigma-Aldrich

(R)-BIDIME

≥97%

Synonym(s):

(R)-3-(tert-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole

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About This Item

Empirical Formula (Hill Notation):
C19H23O3P
CAS Number:
1338454-03-7
Molecular Weight:
330.36
UNSPSC Code:
12352200
NACRES:
NA.22

Quality Level

100

Assay

≥97%

form

powder

optical purity

ee: ≥99% (HPLC)

reaction suitability

reagent type: ligand

functional group

phosphine

Application

(R)-BIDIME is a P-chiral monophosphorus ligand used for the transition metal-catalyzed asymmetric Suzuki-Miyaura and hydroboration reactions.

Other Notes

Synthesis of Chiral α-Amino Tertiary Boronic Esters by Enantioselective Hydroboration of α-Arylenamides

Legal Information

Sold in collaboration with Zejun Pharmaceuticals

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Description
Pricing

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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Wenzhen Fu et al.
Angewandte Chemie (International ed. in English), 54(8), 2520-2524 (2015-01-20)
The first asymmetric nickel-catalyzed intramolecular reductive cyclization of alkynones is reported. A P-chiral monophosphine and triethylsilane were used as the ligand and the reducing reagent, respectively, to form a series of tertiary allylic alcohols bearing furan/pyran rings in excellent yields
Ruofei Cheng et al.
Journal of the American Chemical Society, 140(13), 4508-4511 (2018-03-27)
Carborane cage chirality is an outstanding issue of great interest as the icosahedral carboranes have wide applications in medicinal and materials chemistry. The synthesis of optically active carborane derivatives, whose chirality is associated with the substitution patterns on the polyhedron
Naifu Hu et al.
Journal of the American Chemical Society, 137(21), 6746-6749 (2015-05-06)
The rhodium-catalyzed asymmetric hydroboration of α-arylenamides with BI-DIME as the chiral ligand and (Bpin)2 as the reagent yields for the first time a series of α-amino tertiary boronic esters in good yields and excellent enantioselectivities (up to 99% ee).
Naifu Hu et al.
Angewandte Chemie (International ed. in English), 55(16), 5044-5048 (2016-03-19)
A highly enantioselective alkene aryloxyarylation led to the high-yielding formation of a series of 1,4-benzodioxanes, 1,4-benzooxazines, and chromans containing quaternary stereocenters with excellent enantioselectivity. The sterically bulky and conformationally well defined chiral monophosphorus ligand L4 or L5 was responsible for

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