71663-75-7Relevant articles and documents
A convenient synthesis of N-benzyloxy-β-lactams via N-benzyloxyimines
Ikeda,Achiwa,Sekiya
, p. 1179 - 1184 (2007/10/02)
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FACILE SYNTHESIS OF ALKYL β-BENZYLOXYAMINOCARBOXYLATES RELATED TO MONOCYCLIC β-LACTAMS.
Ikeda, Kiyoshi,Achiwa, Kazuo,Sekiya, Minoru
, p. 4707 - 4710 (2007/10/02)
N-Benzyloxyimines have been shown to react with ketene silyl acetals in the presence of trimethylsilyl triflate catalyst to give alkyl β-benzyloxyaminocarboxylates.Conversion of them to β-lactams has been exemplified.
Titanium Trichloride Reduction of Substituted N-Hydroxy-2-azetidinones and Other Hydroxamic Acids
Mattingly, Phillip G.,Miller, Marvin J.
, p. 410 - 415 (2007/10/02)
A mild method of reduction of the N-O bond of substituted N-hydroxy-2-azetidinones was required to complete a hydroxamic acid mediated synthesis of substituted β-lactams.Of the several reduction methods studied, most either failed to reduce the N-O bond, cleaved the 2-azetidinone ring, or were inefficient and inconvenient.However, buffered titanium trichloride cleanly reduced the N-O bond of the N-hydroxy-2-azetidinones under conditions compatible with a peripheral acid-sensitive tert-butoxycarbonyl (Boc) group and the base-sensitive chiral center at C3.These results therefore constitute an efficient synthesis of β-lactams from substituted serinehydroxamic acids.The competitive C-O and N-O reductions of noncyclic hydroxamic acids of various substitution patterns are also described.
