Alkylation of magnesium enamide with alkyl chlorides and fluorides

Takuji Hatakeyama; Shingo Ito; Masaharu Nakamura; Eiichi Nakamura

doi:10.1021/ja055306q

Alkylation of magnesium enamide with alkyl chlorides and fluorides

Takuji Hatakeyama, Shingo Ito, Masaharu Nakamura^*, Eiichi Nakamura

^*Corresponding author for this work

The University of Tokyo

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

38 Citations (Scopus)

Abstract

A magnesium enamide derived from N-2-(N′,N′-diethylamino)ethyl imine reacts with a primary and secondary alkyl chloride or a primary alkyl fluoride to give an α-alkylated ketone in good to excellent yield after hydrolysis. The reaction takes place with a high level of inversion of stereochemistry at the electrophilic carbon center and will be useful for production of optically active compounds.

Original language	English
Pages (from-to)	14192-14193
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	41
DOIs	https://doi.org/10.1021/ja055306q
Publication status	Published - Oct 19 2005
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja055306q

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abstract = "A magnesium enamide derived from N-2-(N′,N′-diethylamino)ethyl imine reacts with a primary and secondary alkyl chloride or a primary alkyl fluoride to give an α-alkylated ketone in good to excellent yield after hydrolysis. The reaction takes place with a high level of inversion of stereochemistry at the electrophilic carbon center and will be useful for production of optically active compounds.",

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AU - Hatakeyama, Takuji

AU - Ito, Shingo

AU - Nakamura, Masaharu

AU - Nakamura, Eiichi

PY - 2005/10/19

Y1 - 2005/10/19

N2 - A magnesium enamide derived from N-2-(N′,N′-diethylamino)ethyl imine reacts with a primary and secondary alkyl chloride or a primary alkyl fluoride to give an α-alkylated ketone in good to excellent yield after hydrolysis. The reaction takes place with a high level of inversion of stereochemistry at the electrophilic carbon center and will be useful for production of optically active compounds.

AB - A magnesium enamide derived from N-2-(N′,N′-diethylamino)ethyl imine reacts with a primary and secondary alkyl chloride or a primary alkyl fluoride to give an α-alkylated ketone in good to excellent yield after hydrolysis. The reaction takes place with a high level of inversion of stereochemistry at the electrophilic carbon center and will be useful for production of optically active compounds.

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Alkylation of magnesium enamide with alkyl chlorides and fluorides

Abstract

ASJC Scopus Subject Areas

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