Iron-catalysed enantioselective carbometalation of azabicycloalkenes

Laksmikanta Adak; Masayoshi Jin; Shota Saito; Tatsuya Kawabata; Takuma Itoh; Shingo Ito; Akhilesh K. Sharma; Nicholas J. Gower; Paul Cogswell; Jan Geldsetzer; Hikaru Takaya; Katsuhiro Isozaki; Masaharu Nakamura

doi:10.1039/d1cc02387j

Iron-catalysed enantioselective carbometalation of azabicycloalkenes

Laksmikanta Adak, Masayoshi Jin, Shota Saito, Tatsuya Kawabata, Takuma Itoh, Shingo Ito, Akhilesh K. Sharma, Nicholas J. Gower, Paul Cogswell, Jan Geldsetzer, Hikaru Takaya, Katsuhiro Isozaki^*, Masaharu Nakamura

^*Corresponding author for this work

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

7 Citations (Scopus)

Abstract

The first enantioselective carbometalation reaction of azabicycloalkenes has been achieved by iron catalysis toin situform optically active organozinc intermediates, which are amenable to further synthetic elaborations. The observed chiral induction, along with the DFT and XAS analyses, reveals the direct coordination of the chiral phosphine ligand to the iron centre during the carbon-carbon and carbon-metal bond forming step. This new class of iron-catalysed asymmetric reaction will contribute to the synthesis and production of bioactive molecules.

Original language	English
Pages (from-to)	6975-6978
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	57
DOIs	https://doi.org/10.1039/d1cc02387j
Publication status	Published - Jul 21 2021
Externally published	Yes

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry 2021.

ASJC Scopus Subject Areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d1cc02387j

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abstract = "The first enantioselective carbometalation reaction of azabicycloalkenes has been achieved by iron catalysis toin situform optically active organozinc intermediates, which are amenable to further synthetic elaborations. The observed chiral induction, along with the DFT and XAS analyses, reveals the direct coordination of the chiral phosphine ligand to the iron centre during the carbon-carbon and carbon-metal bond forming step. This new class of iron-catalysed asymmetric reaction will contribute to the synthesis and production of bioactive molecules.",

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doi = "10.1039/d1cc02387j",

language = "English",

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T1 - Iron-catalysed enantioselective carbometalation of azabicycloalkenes

AU - Adak, Laksmikanta

AU - Jin, Masayoshi

AU - Saito, Shota

AU - Kawabata, Tatsuya

AU - Itoh, Takuma

AU - Ito, Shingo

AU - Sharma, Akhilesh K.

AU - Gower, Nicholas J.

AU - Cogswell, Paul

AU - Geldsetzer, Jan

AU - Takaya, Hikaru

AU - Isozaki, Katsuhiro

AU - Nakamura, Masaharu

PY - 2021/7/21

Y1 - 2021/7/21

N2 - The first enantioselective carbometalation reaction of azabicycloalkenes has been achieved by iron catalysis toin situform optically active organozinc intermediates, which are amenable to further synthetic elaborations. The observed chiral induction, along with the DFT and XAS analyses, reveals the direct coordination of the chiral phosphine ligand to the iron centre during the carbon-carbon and carbon-metal bond forming step. This new class of iron-catalysed asymmetric reaction will contribute to the synthesis and production of bioactive molecules.

AB - The first enantioselective carbometalation reaction of azabicycloalkenes has been achieved by iron catalysis toin situform optically active organozinc intermediates, which are amenable to further synthetic elaborations. The observed chiral induction, along with the DFT and XAS analyses, reveals the direct coordination of the chiral phosphine ligand to the iron centre during the carbon-carbon and carbon-metal bond forming step. This new class of iron-catalysed asymmetric reaction will contribute to the synthesis and production of bioactive molecules.

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Iron-catalysed enantioselective carbometalation of azabicycloalkenes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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