Ligand-Promoted Asymmetric Imino-Reformatsky Reaction of Ethyl Dibromofluoroacetate

An enantio­selective Reformatsky reaction has been developed for the reaction of ethyl di­bromo­fluoro­acetate (1) with an imine. This method represents the first ligand-promoted imino-Reformatsky approach to use a halo­fluoro­acetate. The use of an amino alcohol ligand allowed for the preparation o...

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Bibliographic Details
Published in:Organic letters 2014-04, Vol.16 (8), p.2080-2083
Main Authors: Tarui, Atsushi, Nishimura, Haruka, Ikebata, Takeshi, Tahira, Asuka, Sato, Kazuyuki, Omote, Masaaki, Minami, Hideki, Miwa, Yoshihisa, Ando, Akira
Format: Article
Language:English
Subjects:
beta-Lactams - chemical synthesis
beta-Lactams - chemistry
Catalysis
Combinatorial Chemistry Techniques
Hydrocarbons, Brominated - chemical synthesis
Hydrocarbons, Brominated - chemistry
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Imines - chemistry
Ligands
Molecular Structure
Stereoisomerism
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Summary:An enantio­selective Reformatsky reaction has been developed for the reaction of ethyl di­bromo­fluoro­acetate (1) with an imine. This method represents the first ligand-promoted imino-Reformatsky approach to use a halo­fluoro­acetate. The use of an amino alcohol ligand allowed for the preparation of enantio­enriched α-bromo-α-fluoro-β-lactams in good yields with enantio­selectivities up to 96% ee. This process also provided access to β-lactam rings bearing two stereo­genic centers.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500631j