Amina

An intramolecular version offers useful synthetic methods for heterocycles. The total syntheses of a- and 7-lycoranes (373 and 374) have been carried out by applying the intramolecular aminochlorination of the carbamate of 5-(2-aminoethyl)-l,3-cyclohexadiene (372) as a key reaction[312,313]. Interestingly, the 4,6- and 5,7-diene amides 375 and 377 undergo the intramolecular amina-tion twice via x-allylpalladium to form alkaloid skeletons ofpyrrolizidine (376) and indolizidine (378), showing that amide group is reactive[314]. 

Amina.tlon, 2-Antinoquinoline [580-22-3] is obtained from quinoline in 80% yield by treatment with barium amide in Hquid ammonia (19). This product, as weU as 3-aminoquinoHne [580-17-6] and 4-antino quinoline [578-68-7], maybe obtained through nucleophilic substitution of the corresponding chloroquinolines with ammonia. 

SOMMELET HAUSER Ammonkjmyfld rearrangement Rearrangement of quaternary ammonium ylids to aminas by aryl trarafer. 

Auch andere Diamine, wie Tetramethyl-athv lendiamin, konnen bei diesem Verfahren verwendet werden (3), nicht jedoch Trialkylamine, da die Addukte A1H3-NR3 (R = CH3, C2H5) im Gegensatz zu den obigen Amina-ten leicht unter H2-Entwicklung bei erhohter Temperatur zerfallen (223). 

Acknowledgments I am grateful for support from a fellowship of the Royal Netherlands Academy of Arts and Sciences, and the exceptional collaborators that make up DART Vanessa Hill Mike Irwin, Pascale Jablonka, Kim Venn, Matthew Shetrone, Amina Helmi, Giuseppina Battaglia, Bruno Letarte, Andrew Cole, Francesca Primas, Patrick Francois, Nobuo Arimoto, Andreas Kaufer, Thomas Szeifert Tom Abel. 

D. A. Evans, K R. Campos, J. S. Tedrow, F. E. Michael, M R. Gagne, Chiral Mixed Phosphorus/Surfur Ligands for Palladium-Catalyzed Allylic Alkylations and Amina-tions, J. Org Chem 1999, 64,2994-2995. 

Identificar los grupos funcionales que caracteri-zan a alcoholes, eteres y aminas. 

Las aminas son compuestos orginicos que con-tienen un itomo de nitrdgeno unido a uno 6 mis itomos de carbono. 

This transformation avoids problems with the change of polarity during the reaction, which occurred in the telomerization, because two aromatic compounds react with each other to form a new aromatic product. The synthesis of 4-nitrodiphenylamine via a Pd-catalyzed Buchwald-Hartwig-type amina-tion from 4-chloronitrobenzene and aniline was chosen as the next test reaction in a cooperation with Lanxess as industrial partner of the network (Scheme 5). 

TABLE 5. O-Silylhydroxylamine-type electrophilic amina-tion reagents... 

Sodium triacetoxyborohhydride is an alternative to NaBH3CN for reductive amina-tion. This reagent can be used with a wide variety of aldehydes and ketones mixed with primary and secondary amines, including aniline derivatives.54 This reagent has been used... 

We did not explore the first of these two approaches too deeply. The synthesis of the epoxide 76, an ideal partner for the alkylation of any trisaccharide amine, was daunting and seemingly difficult but there was available in the literature an excellent route to the enone 77 from tetra-O-benzyl-D-gluconolactone 38 [53]. However, earlier work by Kuzuhara suggested that any reductive amina-tion of the enone 77 would probably proceed in low yield and certainly give a mixture of diastereoisomeric amines [54]. We did prepare the amine 78, via the azide 79, but the amine 78 would not condense with the enone 77 to give the... 

To facilitate accesses to suitably functionalized sialic acid derivatives and complex sialyloligosaccharides for other usehil neoglycoconjugates, phase transfer catalysis (PTC) has been exploited extensively [for reviews see 42]. This process provided a wide range of carbohydrate derivatives under essentially clean Sn2 transformations. In the case of acetochloroneuraminic acid 1, the PTC reactions always provided inverted a-sialic acid derivatives [43]. para-Formylphenyl sialoside 7 [44], together with many other sialoside derivatives such as 8-10 [43], including thioacetate 12 [45] and azide 14 [46], were thus obtained (Scheme 1). Aldehyde 7 and similar glycosides are of particular interest since they could be directly conjugated to protein by reductive amina-tion after suitable deprotection [44]. 

Chiralccl WM Ligand exchange Amina acid-copper... 

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