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693243

(S)-Ru(OAc)2(SEGPHOS®)

Synonym(s):

Diacetato[(S)-(−)-5,5′-bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole]ruthenium(II)

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About This Item

Empirical Formula (Hill Notation):
C42H34O8P2Ru
CAS Number:
373650-12-5
Molecular Weight:
829.73
UNSPSC Code:
12352005
PubChem Substance ID:
329761576
NACRES:
NA.22
MDL number:
MFCD09753024
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form

powder

Quality Level

100

functional group

phosphine

storage temp.

2-8°C

SMILES string

[Ru+2].P(c8ccccc8)(c7ccccc7)c1c(c6c(cc1)OCO6)c2c3c(ccc2P(c5ccccc5)c4ccccc4)OCO3.[O-]C(=O)C.[O-]C(=O)C

InChI

1S/C38H28O4P2.2C2H4O2.Ru/c1-5-13-27(14-6-1)43(28-15-7-2-8-16-28)33-23-21-31-37(41-25-39-31)35(33)36-34(24-22-32-38(36)42-26-40-32)44(29-17-9-3-10-18-29)30-19-11-4-12-20-30;2*1-2(3)4;/h1-24H,25-26H2;2*1H3,(H,3,4);/q;;;+2/p-2

InChI key

BHGLLIGZFQVMBJ-UHFFFAOYSA-L

Application

(S)-Ru(OAc)2(SEGPHOS®) can be used as a catalyst:
  • To prepare highly chemo, enantio, and diastereoselective primary β-amino lactams by asymmetric reductive amination of racemic β-keto lactams.
  • To synthesize chiral primary diarylmethylamines and sterically bulky benzylamines from diaryl and sterically hindered ketones via asymmetric reductive amination reaction.
  • For the conversion of levulinic acid to optically active γ-valerolactone via asymmetric hydrogenation reaction.

Takasago Ligands and Complexes for Asymmetric Reactions

Legal Information

Sold in collaboration with Takasago for research purposes only. JP Registration No. 3148136
SEGPHOS is a registered trademark of Takasago Intl. Corp.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBT2480V
03925LH

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Articles

Takasago Ligands

Hydrogenation, Asymmetric Catalysis, Binap, SEGPHOS®, Aldol reaction, Alkenylation, Arylation, Mannich reaction, Fluorination, Michael addition, Hydrosilylation, Cycloaddition, Takasago

Direct asymmetric reduction of levulinic acid to gamma-valerolactone: synthesis of a chiral platform molecule
Tukacs JM, et al.
Green Chemistry, 17(12), 5189-5195 (2015)
Dynamic Kinetic Asymmetric Reductive Amination: Synthesis of Chiral Primary ?-Amino Lactams
Lou Y, et al.
Angewandte Chemie (International ed. in English), 57(43), 14193-14197 (2018)
Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2
Hu L, et al.
Angewandte Chemie (International Edition in English), 132(13), 5359-5363 (2020)

Global Trade Item Number

SKUGTIN
693243-100MG04061832625270
693243-50MG04061832625287