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693006 Sigma-Aldrich

(S)-SEGPHOS®

≥94%

Synonym: (S)-(−)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole

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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   231-235 °C

Description

Packaging

50, 100 mg in amber 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

Chiral biaryl bisphosphine catalytic ligand used for:
• Rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes
• Stereoselective preparation of homoallylic alcohols via Ir-catalyzed stereoselective transfer hydrogenative crotylation of an allylic acetate with alcohols or aldehydes
• Regio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives
• Diastereo- and enantioselective hydrogenation of α-amino-β-keto ester hydrochlorides catalyzed by an iridium complex
• Preparation of dihydroisoquinolinones via nickel-catalyzed denitrogenative annulation of benzotriazinones with 1,3-dienes and alkenes
• Stereoselective preparation of indanol derivatives via Rh-catalyzed enantioselective alkynylative cyclization of allenyl aldehydes with terminal alkynes

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

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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Description

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905305 (S,S,S)-SPIRAP, ≥95%
905240 (R,R,R)-SPIRAP, ≥95%

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