Advances in Organic Synthesis

Volume: 6

Indexed in: EBSCO, Ulrich's Periodicals Directory

Advances in Organic Synthesis is a book series devoted to the latest advances in synthetic approaches towards challenging structures. It presents comprehensive articles written by eminent authorities ...
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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.