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692395 Sigma-Aldrich

(R)-SEGPHOS®

≥94%

Synonym: (R)-(+)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole, [4(R)-(4,4′-bi-1,3-benzodioxole)-5,5′-diyl]bis[diphenylphosphine]

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes, SEGPHOS More...
InChI Key   RZZDRSHFIVOQAF-UHFFFAOYSA-N
assay   ≥94%
optical activity   [α]20/D +11°, c = 0.5 in chloroform
mp   168-172 °C

Description

Packaging

100 mg in amber glass bottle

50 mg in glass bottle

Legal Information

Sold in collaboration with Takasago for research purposes only. JP Registration No. 3148136

SEGPHOS is a registered trademark of Takasago Intl. Corp.

Application

Takasago Ligands and Complexes for Asymmetric Reactions

Catalytic ligand used for:
• Nickel-catalyzed asymmetric α-arylation and heteroarylation of ketones with chloroarenes
• Enantioselective synthesis of dihydrobenzofurans and dihydronaphthofurans via olefin isomerization/enantioselective intramolecular Alder-ene reaction of enynes catalyzed by Rh
• Preparation of axially chiral biaryl compounds by gold-catalyzed stereoselective intramolecular hydroarylation
• Preparation of chiral silylated homoallylic alcohols and diols by asymmetric addition of alcohols and aldehydes to silylbutadienes catalyzed by ruthenium complexes
• Preparation of chiral 3-alkyl-substituted indolines by tandem condensation-asymmetric hydrogenation of indoles with aldehydes, catalyzed by Bronsted acids and palladium BINAP complexes
• Rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

BINAP/SEGPHOS® Ligands and Complexes

Since the development of BINAP by Noyori 20 years ago, extensive research has been accomplished using this chiral ligand. BINAP proved to be one of the most versatile ligands, catalyzing a wide range...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 3.
Keywords: Addition reactions, Aminations, Arylations, Asymmetric synthesis, Building blocks, Catalysis, Cyclizations, Epoxidations, Hydrogenations, Hydrosilylations, Ligands, Reductive aminations, Sharpless Epoxidation, transformation

Takasago Ligands and Complexes for Asymmetric Reactions

The quest to find chiral catalysts capable of achieving high enantiomeric excess for a variety of asymmetric transformations has been an ongoing endeavor for the past 40 years. One of the most releva...
Keywords: Addition reactions, Arylations, Asymmetric synthesis, Catalysis, Hydrogenations, Ligands, transformation

Related Content

Takasago Ligands - Advantages and Applications

Introduction The quest to find chiral catalysts capable of achieving high enantiomeric excess for a variety of asymmetric transformations has been an ongoing endeavor for the past 40 years. One of th...
Keywords: Addition reactions, Applications, Arylations, Asymmetric synthesis, Building blocks, Catalysis, Epoxidations, Hydrogenations, Hydrosilylations, Ligands, Sharpless Epoxidation, transformation

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