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708682

Sigma-Aldrich

RuCl[(R,R)-TsDPEN](mesitylene)

90%

Synonym(s):

[N-[(1R,2R)-2-(Amino-κN)-1,2- diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro [(1,2,3,4,5,6-η)-1,3,5-trimethylbenzene]-ruthenium

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About This Item

Empirical Formula (Hill Notation):
C30H33ClN2O2RuS
CAS Number:
174813-82-2
Molecular Weight:
622.18
MDL number:
MFCD12545951
UNSPSC Code:
12352116
PubChem Substance ID:
329762817
NACRES:
NA.22

Quality Level

100

Assay

90%

form

solid

mp

241-249 °C

storage temp.

2-8°C

SMILES string

Cc1cc(C)cc(C)c1.Cc2ccc(cc2)S(=O)(=O)N([Ru]Cl)[C@@H]([C@H](N)c3ccccc3)c4ccccc4

InChI

1S/C21H21N2O2S.C9H12.ClH.Ru/c1-16-12-14-19(15-13-16)26(24,25)23-21(18-10-6-3-7-11-18)20(22)17-8-4-2-5-9-17;1-7-4-8(2)6-9(3)5-7;;/h2-15,20-21H,22H2,1H3;4-6H,1-3H3;1H;/q-1;;;+2/p-1/t20-,21-;;;/m1.../s1

InChI key

XBNBOGZUDCYNOJ-AGEKDOICSA-M

Application

Takasago Ligands and Complexes for Asymmetric Reactions
RuCl[(R,R)-TsDPEN](mesitylene) may be used as a catalyst to synthesize:
  • (2R,3S)-4-Benzyl-2-(hydroxyphenylmethyl)morpholin-3-one from racemic N-benzyl-2-benzoyl-3-morpholinone via dynamic kinetic resolution-based asymmetric transfer hydrogenation (ATH).
  • Chiral nonracemic δ-phenylseleno alcohols from δ-phenylseleno ketones via catalytic ATH reaction.

Legal Information

Sold in collaboration with Takasago for research purposes only. WO9720789

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Dynamic Kinetic Resolution-Based Asymmetric Transfer Hydrogenation of 2-Benzoylmorpholinones and Its Use in Concise Stereoselective Synthesis of All Four Stereoisomers of the Antidepressant Reboxetine.
Son SM and Lee HK.
The Journal of Organic Chemistry, 78(17), 8396-8404 (2013)
Stereoselective Synthesis of Substituted Tetrahydropyrans and Isochromans by Cyclization of Phenylseleno Alcohols.
Temperini A, et al.
The Journal of Organic Chemistry, 80(16), 8102-8112 (2015)

Articles

Takasago Ligands

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

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