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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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM4457
MKCH7261
MKBX0847V
MKBT3469V
MKBR1094V

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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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