◆Asymmetric Hydrogenation◆Asymmetric Transfer Hydrogenation

Asymmetric Hydrogenation Catalysts (s-PICA)⚫

Preparation of chiral secondary alcohols⚫

Using hydrogen gas as a hydrogen source⚫

Excellent reactivity and enantioselectiviy⚫

Excellent for bulky acetophenones, ketoesters…

⚫

Very unique substrate scope

Ruthenium Complexes for Asymmetric Hydrogenation

Please see the brochure for details https://www.kanto.co.jp/dcms_media/other/OEA-07_EN.pdf

Typical Procedure & Substrate Scope

RuBr2[(S,S)-dipskewphos](3-amiq) (1.2 mg, 1.0 µmol), t-BuOK (3.4 mg, 31 µmol) and a Teflon coated stirring bar were placedin a 100 mL glass autoclave that had been filled with argon. i-PrOH (0.68 mL) and ketone 1 (0.33 g, 2.0 mmol) were transferred into
the autoclave by a syringe. The solution was degassed by five cycles of vacuum/filling with argon. Hydrogen was initially introduced
into the autoclave at a pressure of 1 MPa then reduced to 0.1 MPa. This procedure was repeated five times. The autoclave wasthen pressurized with H2 gas (1.0 MPa), and the solution was stirred vigorously at 40°C for 21 h. After careful release of thehydrogen, the solution was concentrated to give a crude product. Purification by silica gel column chromatography gave optically
active alcohol 2 (0.33 g, 99%, 98% ee).

Chemoselectivity Control of Ketoesters

Performance of s-PICA

Structure

Product No.

Package

Structure

Product No.

Package

Asymmetric Hydrogenation Catalysts
10535-68

100 mg

Ar = 3,5-(CH3)C6H3
RuBr2[(R,R)-xylskewphos][(R,R)-dpen]

10536-68

100 mg10538-68

100 mg10163-68

100 mg10173-68

100 mg10165-68

100 mg11214-68

100 mg11218-68100 mg

11216-68

100 mg

Ar = 3,5-(CH3)C6H3
RuBr2[(S,S)-xylskewphos][(S,S)-dpen]

10537-68

100 mg

Ar = 3,5-(CH3)C6H3
RuBr2[(R,R)-xylskewphos][(S)-daipen]

Ar = 3,5-(CH3)C6H3
RuBr2[(S,S)-xylskewphos][(R)-daipen]

s-PICA Catalysts
10164-68

100 mg

Ar = 3,5-iPr2C6H3
RuBr2[(R,R)-dipskewphos](3-amiq)

Ar = 3,5-iPr2C6H3
RuBr2[(S,S)-dipskewphos](3-amiq)

10181-68

100 mg

Ar = 3,5-iPr2C6H3
RuBr2[(R,R)-dipskewphos](3,5-dmpica)

Ar = 3,5-iPr2C6H3
RuBr2[(S,S)-dipskewphos](3,5-dmpica)

10166-68

100 mg

Ar = 3,5-iPr2C6H3
RuBr2[(R,R)-dipskewphos](ampz)

Ar = 3,5-iPr2C6H3
RuBr2[(S,S)-dipskewphos](ampz)

11215-68

100 mg

Ar = 3,5-(CH3)C6H3
RuBr2[(R,R)-xylskewphos](3-amiq)

Ar = 3,5-(CH3)C6H3
RuBr2[(S,S)-xylskewphos](3-amiq)

11219-68

100 mg

Ar = 3,5-(CH3)C6H3
RuBr2[(R,R)-xylskewphos](3,5-dmpica)

Ar = 3,5-(CH3)C6H3
RuBr2[(S,S)-xylskewphos](3,5-dmpica)

11217-68
Ar = 3,5-(CH3)C6H3
RuBr2[(R,R)-xylskewphos](ampz)

100 mg
Ar = 3,5-(CH3)C6H3
RuBr2[(S,S)-xylskewphos](ampz)

Structure

Product No.

Package

Structure

Product No.

Package05843-68

200 mg05841-65

200 mg04970-651g04970-55

5g

Chiral Diphosphine Ligands
05842-68

200 mg(R,R)-XylSKEWPHOS(S,S)-XylSKEWPHOS

05840-65

200 mg(R,R)-SKEWPHOS(R)-(+)-BINAP(R)-(+)-Tol-BINAP(R)-(+)-Xyl-BINAP(R)-MeO-F12-BIPHEP(S,S)-SKEWPHOS

04969-651g

04969-55

5g04969-35

25 g

04970-35

25 g41105-651g41106-65

1g41105-55

5g

41106-55

5g

46101-651g46102-65

1g

46101-55

5g

46102-555g

25970-95

200 mg25971-95

200 mg(S)-(−)-BINAP(S)-(−)-Tol-BINAP(S)-(−)-Xyl-BINAP(S)-MeO-F12-BIPHEPAsymmetric Transfer Hydrogenation Catalysts⚫

Preparation of chiral secondary alcohols⚫

Using formate as a hydrogen source⚫

Suitable for base-sensitive ketones⚫

Excellent for cyclic ketones

Chiral Ruthenium Complexes for Asymmetric Transfer HydrogenationPlease see the brochure for details
https://www.kanto.co.jp/dcms_media/other/Modified%20asymetric%20transfer%20hydrogenation%20catalysts%20%26%20Triflate%20catalysts_OEA-03E.pdf

Typical Procedure

To a solution of ketone 1 (1.48 g, 10 mmol) in MeOH (6 mL) was added potassium formate (1.0 g, 12 mmol) and Ru catalyst(6.4 mg, 0.01 mmol) under argon atmosphere. After stirring for 24 h at 50 °C, the reaction was completed (100% conversion) andthe solution was cooled down and diluted with H2O. The solution was extracted with EtOAc, and the combined organic solvent
was concentrated to afford alcohol 2 (99% ee).

Substrate Scope

Large Scale Reaction

Asymmetric Hydrogenation

Structure

Product No.

Package

Structure

Product No.

Package

Modified Asymmetric Transfer Hydrogenation Catalysts
07710-95

200 mg

R = SO2iBu
RuCl[(R,R)-iBuSO2dpen](p-cymene)

07711-95

200 mg07722-95

200 mg07716-95

200 mg07718-95

200 mg07720-95

200 mg07735-95

200 mg07737-95

200 mg

R = SO2iBu
RuCl[(S,S)-iBuSO2dpen](p-cymene)

07721-95

200 mg

R = SO2iBu
RuCl[(R,R)-iBuSO2dpen](mesitylene)

R = SO2iBu
RuCl[(S,S)-iBuSO2dpen](mesitylene)

07715-95

200 mgR = (R)-camphorsulfonyl
RuCl[(R)-Cs-(R,R)-dpen](p-cymene)

R = (S)-camphorsulfonyl
RuCl[(S)-Cs-(S,S)-dpen](p-cymene)

07717-95

200 mg

R = SO2Bn
RuCl[(R,R)-BnSO2dpen](p-cymene)

R = SO2Bn
RuCl[(S,S)-BnSO2dpen](p-cymene)

07719-95

200 mg

R = SO2Bn
RuCl[(R,R)-BnSO2dpen](mesitylene)

R = SO2Bn
RuCl[(S,S)-BnSO2dpen](mesitylene)

07734-95

200 mgR = 2′,6′-(CH3)2Bn

R = 2′,6′-(CH3)2Bn

RuCl[(R,R)-2′,6′-(CH3)2BnSO2dpen](p-cymene)

RuCl[(S,S)-2′,6′-(CH3)2BnSO2dpen](p-cymene)

07736-95

200 mgR = 2′,6′-(CH3)2Bn

R = 2′,6′-(CH3)2Bn

RuCl[(R,R)-2′,6′-(CH3)2BnSO2dpen](mesitylene)

RuCl[(S,S)-2′,6′-(CH3)2BnSO2dpen](mesitylene)

Structure

Product No.

Package

Structure

Product No.

Package

Asymmetric Transfer Hydrogenation Catalysts
08154-95

200 mg08153-95

200 mg08173-95

200 mg08174-95

200 mg08175-95

200 mg08176-95

200 mg41066-95

200 mg41067-95

200 mg41068-95

200 mg41069-95

200 mg

We provide not only reagents, but also bulk chemicals, contract
synthesis, contract development and catalyst screening services.
We are ready to help your research and industrial production.

Our Products (Catalysts and Ligands)
https://www.kanto.co.jp/english/products/organics/organic03.html

Product Examples We can Offer••••

We can also supply these compounds in bulk scale.
Both enantiomers are available.
Only a part of products is listed here.
If you need other compounds, please feel free to contact us.

Ligand Examples We can Offer• Both enantiomers are available.
• Only a part of ligands is listed here.
• If you need other ligands, please feel free to contact us.