Asymmetric Reductive Amination Catalysts for Asymmetric Reductive Amination
–Ir-PSA series–

Ir-PSA

Kanto Chemical has developed novel asymmetric reductive amination catalysts，Ir-PSA for preparation of 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 amines and enantioselective or diastereoselective reduction of pre-prepared imines。These were not efficient methods due to low yield，long steps and poor functional group tolerance。Therefore，we improved our original 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 Ir-PSA and an inexpensive aminoalcohol-based chiral auxiliary enables efficient asymmetric reductive amination of ketones to afford corresponding optically actives in high yield and high stereoselectivity。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 mild oxidative conditions。This method is a practical reaction with excellent functional group tolerance。Ir-PSA are available in both S and R enantiomers。Ir-PSA18is especially effective for the asymmetric reductive amination of phenylacetones，and Ir-PSA36is effective for the 2-tetralones。

Reaction examples by Ir-PSA 18

Reaction examples by Ir-PSA 36

组合式配电装置

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

应用程序到Rotigotine intermediate synthesis

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

应用程序到Tamsulosin intermediate synthesis

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

产品列表

产品，产品	产品，产品	Grade	产品编号。	包装，包装
	（S、S-Ir-PSA18 Chloro[（S、S-N-{1-（4-pyridin-2-yl（2,4,6-trimethylphenyl）methyl}methanesulfonamidato（pentamethylcyclopentadienyl）iridium（III）	asymmetric synthesis	07060-68	100mg
	（R-Ir-PSA18 Chloro[（R-N-{1-（4-pyridin-2-yl（2,4,6-trimethylphenyl）methyl}methanesulfonamidato（pentamethylcyclopentadienyl）iridium（III）	asymmetric synthesis	07071-68	100mg
	（S、S-Ir-PSA36 Chloro[（S、S-N-（1-（4-methoxy-3,5-dimethylpyridin-2-yl）-1-phenylethyl）methanesulfonamidato	asymmetric synthesis	07658-68	100mg
	（R-Ir-PSA36 Chloro[（R-N-（1-（4-methoxy-3,5-dimethylpyridin-2-yl）-1-phenylethyl）methanesulfonamidato	asymmetric synthesis	07035-68	100mg
	L-Valinol		44078-32	25g
			44078-52	5g
	（R）-（-）-2-Amino-3-methyl-1-butanol		42247-2A	5g
	（S、S）-（+）-Phenylglycinol		30757-1A	1g
	D（-）-α-Phenylglycinol		18382-1A	5g
NaIO4个	Sodium periodate	Guaranteed reagent for JIS	37233-00	500克
			37233-20	100g
			37233-30	25g
H5IO6个	方向，方向，方向	Guaranted reagent	32061-30	25g
	（S、S-2-Amino-5-methoxytetralin hydrochloride	asymmetric synthesis	01770-55	5g
	（S、S）-2-Amino-5-methoxytetralin（S、S-mandelate	asymmetric synthesis	01769-55	5g

Patent application by Kanto Chemical Co。

应用程序编号

• WO2014175267
• JP2022-075375
• JP2022-075379

相关信息

• Brochure：
  
  Chiral Amine Synthesis
  
  
• 已释放的页面：
  
  
  “元件”产品面板

公共，公共

• Asymmetric Transfer Hydrogenative Amination of Benzylic Ketones Catalyzed by Cp*Ir（III）Complexes Bearing a ChiralN-（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）。

 

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