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Keywords:

  • asymmetric synthesis;
  • amines;
  • hydrogenation;
  • imines;
  • zinc

Abstract

The first asymmetric hydrogenation/transfer hydrogenation of imines to amines using zinc(II) triflate in combination with chiral ligands is described. The monodentate binaphthophosphepine ligand (3g) provided the highest enantioselectivities. Using different imines, the corresponding amines were obtained in moderate yields and enantioselectivities.

Die ersten asymmetrischen Hydrie rungen bzw. Transfer-hydrierungen von Iminen zu Aminen in Gegenwart von Zinktriflat und chiralen Liganden werden beschrieben. Beste Enantioselektivitäten werden mit dem Binaphthophosphepin-Liganden 3g erhalten. Verschiedene Imine konnten so zu den entsprechenden Aminen mit mo deraten Ausbeuten und Enantioselektivitäten umgesetzt werden.

Featured Compounds

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  1. 1 - 38
Compound 3g
Molecular Weight:368.4505
Molecular Formula:C26H25P
InChIKey:ZSJGLMPHZYLIKA-UHFFFAOYSA-N
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Compound 1a
Molecular Weight:225.2857
Molecular Formula:C15H15NO
InChIKey:WATIYJMFKFSKGZ-FOWTUZBSSA-N
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Compound 2a
Molecular Weight:227.3016
Molecular Formula:C15H17NO
InChIKey:QKBUMGWVDNFABU-UHFFFAOYSA-N
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Compound 2b
Molecular Weight:197.2756
Molecular Formula:C14H15N
InChIKey:IUERBKSXAYWVGE-UHFFFAOYSA-N
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Compound 1b
Molecular Weight:195.2597
Molecular Formula:C14H13N
InChIKey:AVSXJUAELWJJMS-UHFFFAOYSA-N
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Compound 3a
Molecular Weight:426.4694
Molecular Formula:C28H28P2
InChIKey:Not Available
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Compound 3b
Molecular Weight:529.5907
Molecular Formula:C35H33NP2
InChIKey:GYKMEKRMASHMIH-PXLJZGITSA-N
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Compound 3c
Molecular Weight:506.5972
Molecular Formula:C34H36P2
InChIKey:VHHAZLMVLLIMHT-CUPIEXAXSA-N
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Compound 3d
Molecular Weight:756.8477
Molecular Formula:C46H50N2O4P2
InChIKey:JRTHAKOHBMETRC-UHFFFAOYSA-N
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Compound 3e
Molecular Weight:622.6724
Molecular Formula:C44H32P2
InChIKey:Not Available
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Compound 3f
Molecular Weight:340.3973
Molecular Formula:C24H21P
InChIKey:AUWGNKVLUTVYAC-UHFFFAOYSA-N
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Compound 3h
Molecular Weight:359.3576
Molecular Formula:C22H18NO2P
InChIKey:QCHAVHXSBZARBO-UHFFFAOYSA-N
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Compound 3i
Molecular Weight:387.4107
Molecular Formula:C24H22NO2P
InChIKey:SQKCCVLITFBZPD-UHFFFAOYSA-N
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Compound 3j
Molecular Weight:690.7481
Molecular Formula:C44H40N2O2P2
InChIKey:AXMSEDAJMGFTLR-ZAQUEYBZSA-N
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Compound 4a
Molecular Weight:425.5222
Molecular Formula:C27H27N3O2
InChIKey:IYRZZMJRGHERQU-GOTSBHOMSA-N
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Compound 4b
Molecular Weight:369.4159
Molecular Formula:C23H19N3O2
InChIKey:HLHBIMJNCKZZQO-SFTDATJTSA-N
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Compound 4c
Molecular Weight:393.4373
Molecular Formula:C25H19N3O2
InChIKey:BZSJUFJXCHHRHW-LUKWVAJMSA-N
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Compound 4d
Molecular Weight:397.469
Molecular Formula:C25H23N3O2
InChIKey:WAQJMWVRZVOTCH-ZCVTWQBDSA-N
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Compound 4e
Molecular Weight:301.3834
Molecular Formula:C17H23N3O2
InChIKey:CSGQGLBCAHGJDR-HUUCEWRRSA-N
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Compound 5a
Molecular Weight:519.6383
Molecular Formula:C35H29N5
InChIKey:APPVMXCHSLHBIP-XEXPGFJZSA-N
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Compound 5b
Molecular Weight:787.9023
Molecular Formula:C51H41N5O4
InChIKey:BGQQLAIGOCOSQW-KUTKMSJDSA-N
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Compound 6a
Molecular Weight:212.2902
Molecular Formula:C14H16N2
InChIKey:PONXTPCRRASWKW-ZIAGYGMSSA-N
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Compound 6c
Molecular Weight:284.3544
Molecular Formula:C20H16N2
InChIKey:DDAPSNKEOHDLKB-UHFFFAOYSA-N
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Compound 7a
Molecular Weight:373.4272
Molecular Formula:C24H24NOP
InChIKey:OUQSAXROROGQEE-QFIPXVFZSA-N
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Compound 6b
Molecular Weight:244.289
Molecular Formula:C14H16N2O2
InChIKey:MRNPLGLZBUDMRE-ZIAGYGMSSA-N
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Compound 8d
Molecular Weight:752.9589
Molecular Formula:C50H57O4P
InChIKey:AGQAQYPGJDBIQR-UHFFFAOYSA-N
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Compound 8e
Molecular Weight:608.6614
Molecular Formula:C40H33O4P
InChIKey:UQNXHNASBPBCCD-UHFFFAOYSA-N
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Compound 8a
Molecular Weight:700.7152
Molecular Formula:C48H29O4P
InChIKey:QYJHYRSRVCOHMY-UHFFFAOYSA-N
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Compound 8b
Molecular Weight:772.4724
Molecular Formula:C36H17F12O4P
InChIKey:DQORDVSQWPKAQJ-UHFFFAOYSA-N
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Compound 8c
Molecular Weight:865.0671
Molecular Formula:C56H41O4PSi2
InChIKey:BDQOCXQVIFQJRK-UHFFFAOYSA-N
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Compound 8f
Molecular Weight:600.5979
Molecular Formula:C40H25O4P
InChIKey:YKIJNEDTUDPMNC-UHFFFAOYSA-N
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Compound 1
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 2c
Molecular Weight:215.2661
Molecular Formula:C14H14FN
InChIKey:NASFPNSCUMQAOD-UHFFFAOYSA-N
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Compound 2d
Molecular Weight:306.198
Molecular Formula:C15H16BrNO
InChIKey:Not Available
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Compound 2e
Molecular Weight:241.3282
Molecular Formula:C16H19NO
InChIKey:PIJHHFWQTLZEJT-UHFFFAOYSA-N
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Compound 2f
Molecular Weight:303.3975
Molecular Formula:C21H21NO
InChIKey:Not Available
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Compound 2g
Molecular Weight:287.3535
Molecular Formula:C17H21NO3
InChIKey:VRJDVJVTIWPGRD-UHFFFAOYSA-N
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