A Tetradentate Ligand Enables Iron-Catalyzed Asymmetric Hydrogenation of Ketones in a CO- or Isocyanide-Free Fashion

Lei Yang; Xuefeng Tan; Menglong Zhao; Jialin Wen; Xumu Zhang

doi:10.1002/chem.202301609

A Tetradentate Ligand Enables Iron-Catalyzed Asymmetric Hydrogenation of Ketones in a CO- or Isocyanide-Free Fashion

Lei Yang, Xuefeng Tan, Menglong Zhao, Jialin Wen^*, Xumu Zhang^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal Article › peer-review

2 Citations (Scopus)

Abstract

We herein reported the design and synthesis of a ferrocene-based tetradentate ligand that is featured with modular synthesis and rigid skeleton. Its iron(II) complex facilitates asymmetric direct hydrogenation of ketones without the participation of extra strong-field ligand such as CO and isocyanide. Hydride donor lithium aluminum hydride (LAH) converted non-reactive Fe(II) species to reactive Fe(II) hydride species. With this catalyst, various chiral alcohols including the intermediate for montelukast could be prepared with satisfactory yields and enantioinduction.

Original language	English
Article number	e202301609
Journal	Chemistry - A European Journal
Volume	29
Issue number	56
DOIs	https://doi.org/10.1002/chem.202301609
Publication status	Published - 9 Oct 2023
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Keywords

asymmetric hydrogenation
iron catalysis
ketone
strong-field ligand
tetradentate ligand

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10.1002/chem.202301609

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title = "A Tetradentate Ligand Enables Iron-Catalyzed Asymmetric Hydrogenation of Ketones in a CO- or Isocyanide-Free Fashion",

abstract = "We herein reported the design and synthesis of a ferrocene-based tetradentate ligand that is featured with modular synthesis and rigid skeleton. Its iron(II) complex facilitates asymmetric direct hydrogenation of ketones without the participation of extra strong-field ligand such as CO and isocyanide. Hydride donor lithium aluminum hydride (LAH) converted non-reactive Fe(II) species to reactive Fe(II) hydride species. With this catalyst, various chiral alcohols including the intermediate for montelukast could be prepared with satisfactory yields and enantioinduction.",

keywords = "asymmetric hydrogenation, iron catalysis, ketone, strong-field ligand, tetradentate ligand",

author = "Lei Yang and Xuefeng Tan and Menglong Zhao and Jialin Wen and Xumu Zhang",

note = "Publisher Copyright: {\textcopyright} 2023 Wiley-VCH GmbH.",

year = "2023",

month = oct,

day = "9",

doi = "10.1002/chem.202301609",

language = "English",

volume = "29",

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TY - JOUR

T1 - A Tetradentate Ligand Enables Iron-Catalyzed Asymmetric Hydrogenation of Ketones in a CO- or Isocyanide-Free Fashion

AU - Yang, Lei

AU - Tan, Xuefeng

AU - Zhao, Menglong

AU - Wen, Jialin

AU - Zhang, Xumu

PY - 2023/10/9

Y1 - 2023/10/9

N2 - We herein reported the design and synthesis of a ferrocene-based tetradentate ligand that is featured with modular synthesis and rigid skeleton. Its iron(II) complex facilitates asymmetric direct hydrogenation of ketones without the participation of extra strong-field ligand such as CO and isocyanide. Hydride donor lithium aluminum hydride (LAH) converted non-reactive Fe(II) species to reactive Fe(II) hydride species. With this catalyst, various chiral alcohols including the intermediate for montelukast could be prepared with satisfactory yields and enantioinduction.

AB - We herein reported the design and synthesis of a ferrocene-based tetradentate ligand that is featured with modular synthesis and rigid skeleton. Its iron(II) complex facilitates asymmetric direct hydrogenation of ketones without the participation of extra strong-field ligand such as CO and isocyanide. Hydride donor lithium aluminum hydride (LAH) converted non-reactive Fe(II) species to reactive Fe(II) hydride species. With this catalyst, various chiral alcohols including the intermediate for montelukast could be prepared with satisfactory yields and enantioinduction.

KW - asymmetric hydrogenation

KW - iron catalysis

KW - ketone

KW - strong-field ligand

KW - tetradentate ligand

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:001058468600001

U2 - 10.1002/chem.202301609

DO - 10.1002/chem.202301609

M3 - Journal Article

SN - 0947-6539

VL - 29

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 56

M1 - e202301609

ER -

A Tetradentate Ligand Enables Iron-Catalyzed Asymmetric Hydrogenation of Ketones in a CO- or Isocyanide-Free Fashion

Abstract

Bibliographical note

Keywords

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