852693-74-4Relevant academic research and scientific papers
Catalytic, contra-Thermodynamic Positional Alkene Isomerization
Occhialini, Gino,Palani, Vignesh,Wendlandt, Alison E.
, p. 145 - 152 (2022/01/19)
The positional isomerization of C═C double bonds is a powerful strategy for the interconversion of alkene regioisomers. However, existing methods provide access to thermodynamically more stable isomers from less stable starting materials. Here, we report
Application of allylic amine formation from aziridine-2-ol under Appel reaction condition: Synthesis of N-(tert-butoxycarbonyl)-D-vinyl glycine methyl ester
Chavan, Subhash P.,Kawale, Sanket A.,Patil, Niteen B.,Kalbhor, Dinesh B.
supporting information, (2021/05/18)
PPh3/I2/imidazolde mediated allyl amine formation from aziridine-2-alcohol was explored for the synthesis of N-(tert-butoxycarbonyl)-D-vinyl glycine methyl ester.
A convergent synthesis of carbocyclic sinefungin and its C-5 epimer
Ghosh, Arun K.,Lv, Kai
, p. 6761 - 6768 (2016/02/18)
A convergent synthesis of carbocyclic sinefungin (2), its C-5 epimer 3a, and adenine-modified derivative 3b is described. The key features of our approach include the use of commercially available L-methionine and readily available (1R,4S)-4-hydroxy-2-cyclopentenyl acetate as starting materials, a cross-metathesis reaction, an enzymatic kinetic resolution, and a Staudinger reduction. The current synthesis is flexible and, therefore, provides convenient access to the synthesis of various carbocyclic sinefungin analogues for biological evaluation. A convergent synthesis of carbocyclic sinefungin (2), its C-5 epimer 3a, and adenine-modified derivative 3b is described. The key features of this approach include the use of commercially available L-methionine and readily available (1R,4S)-4-hydroxy-2-cyclopentenyl acetate, a cross-metathesis reaction, an enzymatic kinetic resolution, and a Staudinger reduction.
Cross-metathesis of C-allyl iminosugars with alkenyl oxazolidines as a key step in the synthesis of C-iminoglycosyl α-amino acids. A route to iminosugar containing C-glycopeptides
Dondoni, Alessandro,Giovannini, Pier Paolo,Perrone, Daniela
, p. 5508 - 5518 (2007/10/03)
A general access to a novel class of sugar α-amino acids composed of iminofuranose and iminopyranose residues anomerically linked to the glycinyl group through an alkyl chain is described. A set of eight compounds was prepared by the same reaction sequenc
Cross-metathesis of unsaturated α-amino acid derivatives
Biagini, Stefano C. G.,Gibson, Susan E.,Keen, Stephen P.
, p. 2485 - 2499 (2007/10/03)
Cross-metathesis of homoallylglycine derivatives with aryl- and alkyl-substituted alkenes using the ruthenium catalyst (Cy3P)2Cl2Ru=CHPh 1 has been achieved in 43-55 and 55-66% yield respectively. Allylglycine, vinylglycine and dehydroalanine derivatives have also been examined. Whilst cross-metathesis of allylglycine derivatives with alkyl-substituted alkenes using catalyst 1 may be regarded as a synthetically useful procedure, cross-metathesis reactions of vinylglycine and dehydroalanine derivatives using catalyst 1 are non-viable. Attachment of FmocHagOH 13 to a capped Wang resin, cross-metathesis with dodec-1-ene, and product removal from the resin gives the cross-metathesis product in 74% yield based on FmocHagOH.
Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines
Shea, Regan G.,Fitzner, Jeffrey N.,Fankhauser, John E.,Spaltenstein, Andreas,Carpino, Philip A.,et al.
, p. 5243 - 5252 (2007/10/02)
Oxidative rearrangement of allylic selenides in the presence of various amine nucleophiles provides synthetic access to a variety of allylic amine derivatives.The stereochemical outcome of these reactions has been investigated, and is consistent with a -sigmatropic rearrangement mechanism.Several D-α-amino acids and racemic β,γ-unsaturated α-amino acids were prepared in this manner.A variant of this process employing an achiral allylic selenide and chiral amide afforded protected allylic amines in low diastereoisomeric excess.
Synthesis of Protected Racemic β,γ-Unsaturated-α-Amino Acids via γ-Phenylseleno-α,β-Unsaturated Esters
Fitzner, Jeffrey N.,Pratt, Daniel V.,Hopkins, Paul B.
, p. 1959 - 1962 (2007/10/02)
Oxidative rearrangement of γ-phenylseleno-α,β-unsaturated esters (1) with the N-chlorosuccinimide/N,N-diisopropylethylamine/alkyl carbamate reagent combination affords preparatively useful yields of protected β,γ-unsaturated-α-amino acids (2).
