116173-72-9Relevant academic research and scientific papers
Reaction of N-Acyl-α-methoxyamines with Organozic Reagents. A Convenient Method for the Synthesis of Homoallylamines and β-Amino Esters.
Kise, Naoki,Yamazaki, Hiroki,Mabuchi, Toshirou,Shono, Tatsuya
, p. 1561 - 1564 (1994)
The reaction of N-acyl-α-methoxyamines with allyl-, propargyl-, and benzylzinc bromides and Reformatsky reagents proceeds in THF at room temperature.Homoallyl- and homopropargylamines and β-amino esters are synthesized in good yields.
Hofmann-type rearrangement of imides by in situ generation of imide-hypervalent iodines(III) from iodoarenes
Moriyama, Katsuhiko,Ishida, Kazuma,Togo, Hideo
supporting information; experimental part, p. 946 - 949 (2012/05/05)
The Hofmann-type rearrangement of aromatic and aliphatic imides using a hypervalent iodine(III) reagent generated in situ from PhI, m-CPBA, and TsOH·H2O proceeded in the presence of a base in alcohol to provide anthranilic acid derivatives and amino acid derivatives in high yields, respectively. This reaction proceeds through a tandem reaction via alcoholysis followed by a Hofmann rearrangement promoted by the formation of an imide-λ3-iodane intermediate.
Effect of catalytic alkali metal bromide on Hofmann-type rearrangement of imides
Moriyama, Katsuhiko,Ishida, Kazuma,Togo, Hideo
supporting information; experimental part, p. 8574 - 8576 (2012/09/07)
The Hofmann-type rearrangement of aromatic and aliphatic imides using KBr as the catalyst proceeded to provide aromatic and aliphatic amino acid derivatives. We have also developed a new synthetic route to gabapentin with this method.
A new method for the synthesis of β-amino acid derivatives and β- lactams. Reaction of N-alkoxycarbonyl-1-methoxyamines with esters
Kise, Naoki,Ueda, Nasuo
, p. 7511 - 7514 (2007/10/03)
The reaction of N-alkoxycarbonyl-1-methoxyamines with esters is an alternative to the reaction of imines with esters for the synthesis of β- amino acid derivatives. In this reaction, N-alkoxycarbonyl-1-methoxyamines corresponding to unstable imines can also be employed. Although anti adducts were obtained preferentially in the absence of Ti complexes, the diastereoselectivity of this reaction was reversed by the addition of Ti(OPr- i)4. The obtained adducts were transformed to the corresponding β-lactams.
NEW SYNTHESIS OF β-AMINO ACIDS BY NUCLEOPHILIC ADDITION OF ENOLATE ANIONS TO N-METHOXYCARBONYLIMINES GENERATED FROM α-METHOXY CARBAMATES.
Shono, Tatsuya,Kise, Naoki,Sanda, Fumio,Ohi, Satoru,Tsubata, Kenji
, p. 231 - 234 (2007/10/02)
The nucleophilic addition of enolate anions of alkyl acetates to N-methoxycarbonylimines generated from α-methoxy carbamates gave β-amino acid derivates (3) and enantioselective synthesis (72-90percentee) of 3 was achieved by using chiral 2-methyloxazolines instead of acetates.
