Literature DB >> 16218607

Alkylation of magnesium enamide with alkyl chlorides and fluorides.

Takuji Hatakeyama1, Shingo Ito, Masaharu Nakamura, Eiichi Nakamura.   

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 alpha-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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Year:  2005        PMID: 16218607     DOI: 10.1021/ja055306q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  3 in total

1.  Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides.

Authors:  Kaluvu Balaraman; Christian Wolf
Journal:  Org Lett       Date:  2021-11-01       Impact factor: 6.005

2.  Branched-Selective Direct α-Alkylation of Cyclic Ketones with Simple Alkenes.

Authors:  Dong Xing; Xiaotian Qi; Daniel Marchant; Peng Liu; Guangbin Dong
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-21       Impact factor: 15.336

3.  Nickel-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents in the presence of 1,3-butadiene: mechanistic studies of four-component coupling and competing cross-coupling reactions.

Authors:  Takanori Iwasaki; Asuka Fukuoka; Wataru Yokoyama; Xin Min; Ichiro Hisaki; Tao Yang; Masahiro Ehara; Hitoshi Kuniyasu; Nobuaki Kambe
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

  3 in total

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