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Development of a New Heterocycle-Forming Reaction and Kinetic Resolution with N-Heterocyclic Carbenes (Paperback, 1st ed. 2019)
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Development of a New Heterocycle-Forming Reaction and Kinetic Resolution with N-Heterocyclic Carbenes (Paperback, 1st ed. 2019)
Series: Springer Theses
Expected to ship within 10 - 15 working days
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In this book, the author focuses on exploring new organocatalytic
transformations under operationally simple and environmentally
friendly reaction conditions. Two new types of catalytic reactions
promoted by N-heterocyclic carbenes (NHCs) are described. The oxa-
and azacycle-forming reactions of sulfonylalkynols and
sulfonylalkynamides are broadly considered to be a new type of
activation mode in NHC chemistry, wherein the bond formation with
internal O- and N-nucleophiles occurs at the -position of the
propargyl sulfones with 1,2-sulfonyl migration. The resulting oxa-
and azacycles are core structures in many biologically significant
compounds and medicinally important agents. In addition, the book
develops the chiral NHC-catalyzed kinetic resolution of -hydroxy
carboxylic acid derivatives based on chiral recognition of the
substrate-cocatalyst complex. In this carboxylate
cocatalyst-assisted chiral acylation, the reaction rate
acceleration and selectivity enhancement are interpreted in terms
of the reversible complexation of the substrate and carboxylate
cocatalyst, which is verified by control experiments and measured
using analytical methods. The findings described here reveal a
promising new aspect of not only NHC catalysis but also identifying
novel catalysis systems.
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