The palladium-catalyzed
aminoazidation of aminoalkenes yielding
azidomethyl-substituted nitrogen-containing heterocycles was developed.
The procedure requires oxidative conditions and occurs at room temperature
in the presence of hydrogen peroxide and NaN3 as the azide
source. These conditions provide selective exo-cyclization/azidation
of the carbon–carbon double bond, furnishing a versatile approach
toward five-, six-, and seven-membered heterocyclic rings.
Treatment of O-allyl N-tosyl carbamates with aromatic compounds in the presence of Cu(OTf)2 or TMSOTf as promoters, affords N-substituted 1-arylpropan-2-amines, 1,2-diarylpropanes, 1,1-diarylpropanes, or indanes, depending on the nature of the...
Dedicated to Prof. Franco Cozzi for its 70th birthday.The main goal in developing peptidomimetics is the stabilization of the bioactive conformation of peptides. Among all the secondary structures, turns are of paramount importance. This review highlights the recent advances in the design and synthesis of cyclic turn mimics. Both amino acids, carbo-and hetero-cyclic scaffolds have been considered, focusing on their use in the preparation of peptidomimetics and on their ability to induce γ-, β-, and α-turns.
A useful aminohalogenation reaction for the cyclization of O‐alkynyl carbamates under copper catalysis has been developed. N‐Halosuccinimides have been used as a halogen source. The intramolecular C−N bond formation occurs selectively affording haloalkylidene substituted heterocycles. Just in the case of α,α‐cyclohexyl‐substituted propargyl carbamate, the alkoxyhalogenation pathway was operative. The mechanism for the two alternative reaction pathways was investigated by modeling the corresponding transition states at the DFT level.
A wide range of methodologies for the preparation of organic azides has been reported in the literature for many decades, due to their interest as building blocks for different transformations and their applications in biology as well as in materials science. More recently, with the spread of the use of transition metal-catalyzed reactions, new perspectives have also materialized in azidation processes, especially concerning the azidation of C–H bonds and direct difunctionalization of multiple carbon-carbon bonds. In this review, special emphasis will be placed on reactions involving substrates bearing a leaving group, hydroazidation reactions and azidation reactions that proceed with the formation of more than one bond. Further reactions for the preparation of allyl and vinyl azides as well as for azidations involving the opening of a ring complete the classification of the material.
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