Exo-Cyclization: Intermolecular Methylene Transfer Sequence in Au-Catalyzed Reactions of O-Homopropargylic Oximes

Itaru Nakamura; Arinobu Hirayama; Shinya Gima; Masahiro Terada

doi:10.1002/chem.202002764

Exo-Cyclization: Intermolecular Methylene Transfer Sequence in Au-Catalyzed Reactions of O-Homopropargylic Oximes

Itaru Nakamura, Arinobu Hirayama, Shinya Gima, Masahiro Terada

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

Abstract

The Au-catalyzed reactions of O-homopropaylic oximes afforded the 3-alkenylated isoxazolines in good to high yields. The mechanistic studies suggest that the reaction proceeds through an exo-cyclization followed by intermolecular methylene group transfer. In addition, oligomeric species of the starting material were observed in the reaction mixture by mass spectra, supporting our proposed mechanism, which proceeds through a repeated intermolecular C−C bond forming process.

Original language	English
Journal	Chemistry - A European Journal
DOIs	https://doi.org/10.1002/chem.202002764
Publication status	Accepted/In press - 2020

Keywords

alkynes
cascade reactions
gold catalysts
heterocycles
rearrangement

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "Exo-Cyclization: Intermolecular Methylene Transfer Sequence in Au-Catalyzed Reactions of O-Homopropargylic Oximes",

abstract = "The Au-catalyzed reactions of O-homopropaylic oximes afforded the 3-alkenylated isoxazolines in good to high yields. The mechanistic studies suggest that the reaction proceeds through an exo-cyclization followed by intermolecular methylene group transfer. In addition, oligomeric species of the starting material were observed in the reaction mixture by mass spectra, supporting our proposed mechanism, which proceeds through a repeated intermolecular C−C bond forming process.",

keywords = "alkynes, cascade reactions, gold catalysts, heterocycles, rearrangement",

author = "Itaru Nakamura and Arinobu Hirayama and Shinya Gima and Masahiro Terada",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP17H06447 (Grant‐in‐Aid for Scientific Research on Innovative Areas “Hybrid Catalysis for Enabling Molecular Synthesis on Demand”) and JP20H02731 (Grant‐in‐Aid for Scientific Research (B)) from MEXT Japan. ",

year = "2020",

doi = "10.1002/chem.202002764",

language = "English",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

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TY - JOUR

T1 - Exo-Cyclization

T2 - Intermolecular Methylene Transfer Sequence in Au-Catalyzed Reactions of O-Homopropargylic Oximes

AU - Nakamura, Itaru

AU - Hirayama, Arinobu

AU - Gima, Shinya

AU - Terada, Masahiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP17H06447 (Grant‐in‐Aid for Scientific Research on Innovative Areas “Hybrid Catalysis for Enabling Molecular Synthesis on Demand”) and JP20H02731 (Grant‐in‐Aid for Scientific Research (B)) from MEXT Japan.

PY - 2020

Y1 - 2020

N2 - The Au-catalyzed reactions of O-homopropaylic oximes afforded the 3-alkenylated isoxazolines in good to high yields. The mechanistic studies suggest that the reaction proceeds through an exo-cyclization followed by intermolecular methylene group transfer. In addition, oligomeric species of the starting material were observed in the reaction mixture by mass spectra, supporting our proposed mechanism, which proceeds through a repeated intermolecular C−C bond forming process.

AB - The Au-catalyzed reactions of O-homopropaylic oximes afforded the 3-alkenylated isoxazolines in good to high yields. The mechanistic studies suggest that the reaction proceeds through an exo-cyclization followed by intermolecular methylene group transfer. In addition, oligomeric species of the starting material were observed in the reaction mixture by mass spectra, supporting our proposed mechanism, which proceeds through a repeated intermolecular C−C bond forming process.

KW - alkynes

KW - cascade reactions

KW - gold catalysts

KW - heterocycles

KW - rearrangement

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