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Hydrazones as Singular Reagents in Asymmetric Organocatalysis
Author(s) -
de Gracia Retamosa María,
Matador Esteban,
Monge David,
Lassaletta José M.,
Fernández Rosario
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602430
Subject(s) - electrophile , synthon , organocatalysis , nucleophile , reagent , chemistry , cycloaddition , combinatorial chemistry , reactivity (psychology) , enantioselective synthesis , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
This Minireview summarizes strategies and developments regarding the use of hydrazones as reagents in asymmetric organocatalysis, their distinct roles in nucleophile–electrophile, cycloaddition, and cyclization reactions. The key structural elements governing the reactivity of these reagents in a preferred pathway will be discussed, as well as their different interactions with organocatalysts, leading to diverse activation modes. Along these studies, the synthetic equivalence of N ‐monoalkyl, N , N ‐dialkyl, and N ‐acyl hydrazones with several synthons is also highlighted. Emphasis is also put on the mechanistic studies performed to understand the observed reactivities. Finally, the functional group transformations performed from the available products has also been analyzed, highlighting the synthetic value of these methodologies, which served to access numerous families of valuable multifunctional compounds and nitrogen‐containing heterocycles.