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 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.
Faculty of Pharmaceutical Sciences, Setsunan University , 45-1 Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan.
Atsushi
A
Tarui
Haruka
H
Nishimura
Takeshi
T
Ikebata
Asuka
A
Tahira
Kazuyuki
K
Sato
Masaaki
M
Omote
Hideki
H
Minami
Yoshihisa
Y
Miwa
Akira
A
Ando
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D013237:Stereoisomerism; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated; D007097:Imines; D008024:Ligands; D047090:beta-Lactams