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May 13-14, 2019 | Prague, Czech Republic
Chemistry and Medicinal Chemistry
9th World Congress on
Page 47
Asian Journal of Biomedical and Pharmaceutical Sciences | Volume 9 ISSN: 2249-622X
Vanya Kurteva
Bulgarian Academy of Sciences, Bulgaria
Chiral anime induced enantioselectivity in trans-β-lactam formation
via Staudinger Cycloaddition
Azetidine-2-ones, so-called β-lactams, are heterocyclic
systems of great importance as they exist as structural
subunits in many products of interest as pharmaceuticals,
catalysts, synthetic building blocks. The subsequent
development of a number of classes of β-lactam antibiotics
has made this family of four-membered ring amides one of
the most successful classes of therapeutic agents to date.
The stereoisomerically pure azetidinones receive special
attention as the ring stereochemistry is closely related
with their biological activities. Beta-lactam antibiotic
families with trans configuration of azetidinone ring, like
penems, carbapenems, thienamycines, trinems, cephems,
oxacephems, azacephems, etc., have shown extraordinary
broad spectrum of activities against aerobic and anaerobic
gram-positive and gram-negative organisms.
The stereoselectivity induced during the azetidinone
ring construction represents a key element. Despite the
diversity of the synthetic protocols developed, the classical
Staudinger [2+2] ketene-imine cycloaddition reaction
is still of the day and is widely exploited, especially in its
asymmetric version by applying chiral auxiliaries. Among
the latter, chiral ketene precursors are the most widely
applied, while the records in the literature on the efficiency
of chiral amines are quite limited. Recently, we reported
on the enantioselective trans-β-lactam synthesis driven
by variable commercial chiral amines and showed that the
selectivity is strongly dependent both on chiral auxiliary
and type, position and number of substituents at aromatic
aldehyde unit, i.e. no universal auxiliary is discovered.
This talk will summarize the results on the efficiency of
various chiral amines as auxiliaries in the enantioselective
construction of trans-β-lactam ring via Staudinger
cycloaddition.
Speaker Biography
Vanya Kurteva, Prof. Dr. Organic Chemistry, has her expertise in organic
synthesis and catalysis. Her team is developed efficient protocols for
construction of 2,3-disubstituted imidazo[1,2-a]-pyridines, pirlindole
derivatives, N, O-macrocycles, azo-naphthol dyes, etc., as well as
various polydentate ligands as synergists and extractants for isolation
and separation of metal ions. She spent a research period in the
laboratory of Prof. Carlos Afonso (Lisbon, Portugal) working on the
synthesis of cyclopentitols, microwave assisted transformations, and
reactions in chiral ionic liquids. Her current research interests are
focused mainly on the synthesis of heterocycles with potential interest
as chemotherapeutics and ligands for coordination applications. She is
a professor and vice-director of the Institute of Organic Chemistry with
Centre of Phytochemistry, Bulgarian Academy of Sciences.
e:
Vanya Kurteva, Asian J Biomed Pharmaceut Sci, Volume:9
DOI: 10.4066/2249-622X-C2-019
Notes: