37479-38-2Relevant academic research and scientific papers
Stereoselective synthesis of trans- and cis-2-aryl-3-(hydroxymethyl) aziridines through transformation of 4-aryl-3-chloro-β-lactams and study of their ring opening
D'Hooghe, Matthias,Mollet, Karen,Dekeukeleire, Stijn,De Kimpe, Norbert
experimental part, p. 607 - 615 (2010/04/30)
trans- and cis-1-Alkyl-4-aryl-3-chloroazetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were transformed into the corresponding non-activated trans- and cis-2-aryl-3-(hydroxymethyl)aziridines via reductive ring contraction using LiAlH4 in Et2O. Furthermore, trans-2-aryl-3- (hydroxymethyl)aziridines were transformed into 2-amino-3-arylpropan-1-ols and anti-2-amino-3-aryl-3-methoxypropan-1-ols by means of an unprecedented ring opening by LiAlH4 and by MeOH, respectively. cis-2-Aryl-3- (hydroxymethyl)aziridines were shown to be highly reluctant to undergo ring opening by LiAlH4 and MeOH under similar reaction conditions.
Aziridines as templates: A general strategy for the stereospecific synthesis of 2-azetidinones
Sharma,Kanwar, Seema,Rajpoot, Shivani
, p. 11 - 19 (2007/10/03)
Various routes to a variety of azridine-2-carboxylates have been described and the stereochemistry of these compounds has been determined by spectroscopic methods. Further, greater diversity of β-lactams via ring expansion of these azridines-2-carboxylates were obtained by a general, efficient and direct stereospecific approach.
The halogen-lithium exchange reaction of 3,3-dichloro-2-azetidinones: Application to the synthesis of cis-4-aryl-3-chloro-2-azetidinones
Dejaegher, Yves,Denolf, Bram,Stevens, Christian V.,De Kimpe, Norbert
, p. 193 - 198 (2007/10/03)
A straightforward synthesis of new cis-4-aryl-3-chloro-2-azetidinones was developed, using a halogen-lithium exchange reaction on 4-aryl-3,3-dichloro-2- azetidinones. This methodology was further extended to the use of alkyl halides as electrophiles, while more complex electrophiles could not be introduced.
ELECTROCHEMICAL STUDIES ON Β-LACTAMS. PART 4. ELECTROACETYLATION OF Β-LACTAMS.
Casadei, Maria Antonietta,Inesi, Achille,Moracci, Franco Micheletti,Occhialini, Donatella
, p. 6885 - 6890 (2007/10/02)
Electroreduction of 3-bromo- and 3,3-dichloro-β-lactams 1 carried out at the potential of the first voltammetric peak and in the presence of acetic anhydride gives 3-acetyl-β-lactams 2.The electrosynthesis is highly stereoselective, as only the acetyl der
