Chiral Perazamacrocycles: Synthesis and Applications. Part 1
Pp. 115-166 (52)
Diego Savoia and Andrea Gualandi
Chiral non-racemic perazamacrocyles containing three or more nitrogen atoms
in the form of different functions (amine, amide, imine) are prepared from optically active
amines, diamines, α-aminoacids, and their derivatives, by properly selected methodologies.
The many applications of these optically pure perazamacrocycles rely on the basic and/or
hydrogen bond donor properties of the nitrogen functions and include metal ions
coordination, supramolecular chemistry, material science, molecular and enantioselective
recognition, and asymmetric catalysis. Part 1 describes the preparation of polyamino,
poly(amino-amido), polyamido macrocycles by procedures involving mainly nucleophilic
substitution and acylation reactions, but also ring closing metathesis, multicomponent and
click reactions in the cyclization step.
Acylic nucleophilic substitution, aldol condensation, alkyne-azide
cycloaddition (click reaction), amides, amines, asymmetric synthesis, atkinsrichman
procedure, aziridine ring opening, bridged macropolycycles, chiral
stationary phase, chiral perazamacrocycle, cyclam, cyclization, cyclophane,
cyclopolypeptide, enantioselective catalysis, enantioselective recognition,
epoxidation, ex-chiral pool synthesis, guanidinium macrocycles, henry reaction,
imines, lactamization, metal complexes, metal ion coordination, mitsunobu
reaction, molecular knot, molecular recognition, multicomponent reaction,
nitrogen ligands, nucleophilic substitution, on-resin synthesis, perazamacrocycles,
pseudopolypeptide, radiopharmaceutical, receptor (macrocyclic), reductive
coupling, reduction, ring closing metathesis, ring closure, ring opening,
superoxide dismutase mimics, supramolecular chemistry, ugi reaction.
Dipartimento di Chimica "G. Ciamician", Università di Bologna, via Selmi 2, 40126 Bologna, Italy.