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692980 Sigma-Aldrich

(S)-DTBM-SEGPHOS®

≥94%

Synonym: (S)-(+)-5,5′-Bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4′-bi-1,3-benzodioxole

  • CAS Number 210169-40-7

  • Empirical Formula (Hill Notation) C74H100O8P2

  • Molecular Weight 1179.53

  •  MDL number MFCD09753003

  •  PubChem Substance ID 329761548

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes, SEGPHOS More...
assay   ≥94%
SMILES string   COc1c(cc(cc1C(C)(C)C)P(c2cc(c(OC)c(c2)C(C)(C)C)C(C)(C)C)c3ccc4OCOc4c3-c5c6OCOc6ccc5P(c7cc(c(OC)c(c7)C(C)(C)C)C(C)(C)C)c8cc(c(OC)c(c8)C(C)(C)C)C(C)(C)C)C(C)(C)C
InChI   1S/C74H100O8P2/c1-67(2,3)47-33-43(34-48(61(47)75-25)68(4,5)6)83(44-35-49(69(7,8)9)62(76-26)50(36-44)70(10,11)12)57-31-29-55-65(81-41-79-55)59(57)60-58(32-30-56-66(60)82-42-80-56)84(45-37-51(71(13,14)15)63(77-27)52(38-45)72(16,17)18)46-39-53(73(19,20)21)64(78-28)54(40-46)74(22,23)24/h29-40H,41-42H2,1-28H3
InChI key   ZNORAFJUESSLTM-UHFFFAOYSA-N

Description

Application

Takasago Ligands and Complexes for Asymmetric Reactions

Catalytic ligand for:
• Enantioselective synthesis of secondary allylic alcohols via enantioselective reductions of α,β-unsaturated ketones
• Stereoselective preparation of cyclohexanone derivatives via rhodium-catalyzed rearrangement of allyl or allenic cyclobutanols
• Cu-catalyzed asymmetric conjugate reduction of beta-substituted unsaturated phosphonates to give optically active beta-stereogenic alkylphosphonates
• Asymmetric synthesis of cyclohexenones via Rh-catalyzed desymmetrization through enantioselective C-C bond activation and ring expansion of allenyl cyclobutanols
• Enantioselective synthesis and crystal structure of P-stereogenic alkynylphosphine oxides by Rh-catalyzed [2+2+2] cycloaddition

Packaging

1 g in glass bottle

50, 100 mg in glass insert

Legal Information

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

SEGPHOS is a registered trademark of Takasago Intl. Corp.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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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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