1225547-90-9Relevant academic research and scientific papers
Ni-catalyzed α-arylation of secondary α-bromo-α-fluoro- β-lactam: Cross-coupling of a secondary fluorine-containing electrophile
Tarui, Atsushi,Kondo, Shoji,Sato, Kazuyuki,Omote, Masaaki,Minami, Hideki,Miwa, Yoshihisa,Ando, Akira
, p. 1559 - 1565 (2013)
A highly diastereoselective cross-coupling reaction of an α-bromo-α-fluoro-β-lactam with a wide range of aryl Grignard reagents was catalyzed by Ni/bis(oxazoline) in yields of up to 98%. The product was obtained diastereoselectively as an anti-isomer. This is the first successful α-arylation of an α-fluoro-β-lactam to produce diverse α-aryl-α-fluoro-β-lactams.
Diethylzinc-mediated addition of 2,2-dibromo-2-fluoroacetamides to carbonyl compounds: Synthesis of α-bromo-α-fluoro-β-hydroxy amides and/or (Z)-fluorovinyl amides
Lemonnier, Gerald,Poisson, Thomas,Couve-Bonnaire, Samuel,Jubault, Philippe,Pannecoucke, Xavier
, p. 3278 - 3289 (2013/06/27)
We describe straightforward routes either to α-bromo-α-fluoro- β-hydroxy amides or to (Z)-α-fluoroacrylamides starting from aldehydes, ketones or imine and 2,2-dibromo-2-fluoroacetamides. Depending on the nature of the amide, these diethylzinc-mediated additions to aldehydes, ketones or imine afford selective access either to bromofluorohydrins or to (Z)-α-fluoroacrylamides. The corresponding products were obtained in moderate to very good yields and the configurations of both products were confirmed by X-ray analyses. Reactions between aldehydes, ketones or imines and 2,2-dibromo-2-fluoroacetamides, a new class of fluorinated reagent, allow straightforward selective access to α-bromo-α-fluoro-β-hydroxy amides and/or (Z)-α-fluoroacrylamides with moderate to excellent yields. Copyright
Simple, chemoselective, and diastereoselective Reformatsky-type synthesis of α-bromo-α-fluoro-β-lactams
Tarui, Atsushi,Kawashima, Naoto,Sato, Kazuyuki,Omote, Masaaki,Miwa, Yoshihisa,Minami, Hideki,Ando, Akira
supporting information; experimental part, p. 2000 - 2003 (2010/06/21)
The chemoselective and diastereoselective synthesis of syn-α-bromo-α-fluoro-β-lactams was achieved using the diethylzinc-mediated Reformatsky-type reaction of ethyl dibromofluoroacetate with imines. The reaction led to diastereomerically pure β-lactams in good to moderate yields (up to 78% yield) with only small amounts of aziridine derivatives. Noncyclized 3-amino-2-bromo-2-fluoro carboxylic esters, usual Reformatsky adducts, were not formed. In contrast, reactions carried out under typical Reformatsky conditions using zinc metal were poorly chemoselective, leading to mixtures of β-lactams and aziridine derivatives.
