An expedient, stereoselective synthesis of highly functionalized cyclic compounds

2002 ◽  
Vol 26 (12) ◽  
pp. 1753-1767 ◽  
Author(s):  
Ewa Krawczyk ◽  
Krzysztof Owsianik ◽  
Aleksandra Skowrońska ◽  
Michał Wieczorek ◽  
Wiesław Majzner
ChemInform ◽  
2010 ◽  
Vol 33 (15) ◽  
pp. no-no
Author(s):  
Hitoshi Akiyama ◽  
Tetsuya Fujimoto ◽  
Katsuyoshi Ohshima ◽  
Kenji Hoshino ◽  
Yuko Saito ◽  
...  

ChemInform ◽  
2010 ◽  
Vol 31 (23) ◽  
pp. no-no
Author(s):  
Carlos Cativiela ◽  
Maria Dolores Diaz-de-Villegas

2020 ◽  
Vol 24 (18) ◽  
pp. 2169-2180
Author(s):  
Atsushi Tarui ◽  
Yukiko Karuo ◽  
Kazuyuki Sato ◽  
Kentaro Kawai ◽  
Masaaki Omote

β-Lactams, found in β -lactam antibiotics, are the structurally distorted cyclic compounds being subjected to nucleophilic acyl substitution reaction. α-Fluorination of β -lactams is a simple and expedient approach to control the reactivity of β-lactam ring toward nucleophilic attack, which would hopefully lead to the new design of future antibiotics. From the viewpoint of obtaining multisubstituted α -fluoro-β-lactams, α -bromo-α- fluoro-β-lactams are considered as key compounds for structure functionalization, including nucleophilic substitution reaction, aldol-type reaction and metal-catalyzed crosscoupling reaction. All the reactions can be conducted smoothly to afford a variety of multisubstituted α-fluoro-β-lactams. During the course of the examination, chiral α,α-difluoro- β-lactams and α -bromo-β-fluoro-α-lactams are successfully obtained, which are considered potent precursors for making stereocontrolled multisubstituted α-fluoro-β-lactams.


2000 ◽  
Vol 11 (3) ◽  
pp. 645-732 ◽  
Author(s):  
Carlos Cativiela ◽  
Marı́a Dolores Dı́az-de-Villegas

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