2022/10/06

Catalysts for Asymmetric Reductive Amination –Ir-PSA series–Ir-PSA
Kanto Chemical has developed novel asymmetric reductive amination catalysts, Ir-PSA for preparationof optically active amines.
Optically active amines are important compounds such as intermediates of pharmaceuticals.
Conventional methods for synthesis of optically active amines include optical resolution of racemic aminesand enantioselective or diastereoselective reduction of pre-prepared imines. These were not efficientmethods due to low yield, long steps and poor functional group tolerance. Therefore, we improved ouroriginal reductive amination catalysts (Ir-PA, Ir-QN) into asymmetric catalysts (Ir-PSA) and developed
an efficient method for preparation of optically active amines. In this method, combination of chiral IrPSA and an inexpensive aminoalcohol-based chiral auxiliary enables efficient asymmetric reductive
amination of ketones to afford corresponding optically active amines in high yield and highstereoselectivity. It is especially effective for amines that are difficult to obtain by conventional
asymmetric synthesis. And the aminoalcohol moiety can be easily and quantitatively removed under mildoxidative conditions. This method is a practical reaction with excellent functional group tolerance. Ir-PSA
are available in both S and R enantiomers. Ir-PSA18 is especially effective for the asymmetric reductive
amination of phenylacetones, and Ir-PSA36 is effective for the 2-tetralones.

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Reaction examples by Ir-PSA18

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Reaction examples by Ir-PSA36

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Comparison with other asymmetric reductive aminations

This method exhibits superior stereoselectivity compared to sodium borohydride reduction and Pd
catalytic hydrogenation.

Application to Rotigotine intermediate synthesis

The optical purity can be easily increased by recrystallization of the diastereomeric intermediate.

Application to Tamsulosin intermediate synthesis

Process shortening and cost reduction can be expected in optically active amine synthesis.

Product list
Product(S)-Ir-PSA18
Chloro[(S)-N-{1-(4-pyridin-2-yl(2,4,6trimethylphenyl)methyl}methanesulfonamidato](pentamethylcyclopentadienyl)iridium(III)(R)-Ir-PSA18
Chloro[(R)-N-{1-(4-pyridin-2-yl(2,4,6trimethylphenyl)methyl}methanesulfonamidato](pentamethylcyclopentadienyl)iridium(III)

GradeProductNo.

Packageforasymmetric07060-68

100 mg07071-68

100 mg07658-68

100 mg07035-68

100 mgsynthesisforasymmetricsynthesis(S)-Ir-PSA36
Chloro[(S)-N-(1-(4-methoxy-3,5-fordimethylpyridin-2-yl)-1-asymmetricphenylethyl)methanesulfonamidato](pentame

synthesis

thylcyclopentadienyl)iridium(III)(R)-Ir-PSA36
Chloro[(R)-N-(1-(4-methoxy-3,5-fordimethylpyridin-2-yl)-1-asymmetricphenylethyl)methanesulfonamidato](pentame

synthesis

thylcyclopentadienyl)iridium(III)ProductGradeProductNo.

Package44078-32

25 g44078-525g(R)-(-)-2-Amino-3-methyl-1-butanol

42247-2A

5g(S)-(+)-Phenylglycinol

30757-1A

1g

18382-2A

25 g

18382-1A

5g

37233-00

500 g

37233-20

100 g37233-30

25 g32061-30

25 g

01770-555g01769-55

5g

L-Valinol

D(-)-α- Phenylglycinol

Guaranteed
NaIO4Sodium periodate

reagent forJIS

H5IO6

Orthoperiodic acid(S)-2-Amino-5-methoxytetralinhydrochloride(S)-2-Amino-5-methoxytetralin(S)mandelate

Patent application by Kanto Chemical Co.
Application number

WO2014175267

JP2022-075375

JP2022-075379

Guaranteedreagent
forasymmetricsynthesis
forasymmetricsynthesis

Related Information
Brochure:
Iridium Catalyst for Chiral Amine Synthesis
Related Page:"Catalysts" Product PagePublications


Asymmetric Transfer Hydrogenative Amination of Benzylic Ketones Catalyzed by Cp*Ir(III)Complexes Bearing a Chiral N-(2-Picolyl)sulfonamidato Ligand
T.Kawada, K.Yabushita, T.Yasuda, T.Ohta, T.Yajima, K.Tanaka, N.Utsumi, M.Watanabe, K.Murata,
Y.Kayaki, S.Kuwata, and T.Katayama
The Journal of Organic Chemistry, 87(13), 8458-8468(2022)

Development of an Efficient Method for the Synthesis of Chiral Amines by Using New Chiral Iridium
Catalyst.
T.Kawada, T.Katayama
THE CHEMICAL TIMES, 264, 26-31 (2022).

REAGENT DIVISION
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TEL: +81-3-6214-1092

Website : https:/www.kanto.co.jp